2-Cyclohexen-1-ol, 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[[(1,1-dimethylethyl)diphenylsil yl]oxy]methyl]-5-(2-hydroxyethylidene)-4-[(phenylmethoxy)methoxy]-, (1S,4R,5E,6R)-

Base Information

• Chemical Name: 2-Cyclohexen-1-ol, 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[[(1,1-dimethylethyl)diphenylsil yl]oxy]methyl]-5-(2-hydroxyethylidene)-4-[(phenylmethoxy)methoxy]-, (1S,4R,5E,6R)-
• CAS No.: 588693-71-4
• Molecular Formula: C38H48O7Si
• Molecular Weight: 644.88
• Mol file: 588693-71-4.mol

Synonyms:

Chemical Property of 2-Cyclohexen-1-ol, 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[[(1,1-dimethylethyl)diphenylsil yl]oxy]methyl]-5-(2-hydroxyethylidene)-4-[(phenylmethoxy)methoxy]-, (1S,4R,5E,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Cyclohexen-1-ol, 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[[(1,1-dimethylethyl)diphenylsil yl]oxy]methyl]-5-(2-hydroxyethylidene)-4-[(phenylmethoxy)methoxy]-, (1S,4R,5E,6R)-

There total 9 articles about 2-Cyclohexen-1-ol, 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[[[(1,1-dimethylethyl)diphenylsil yl]oxy]methyl]-5-(2-hydroxyethylidene)-4-[(phenylmethoxy)methoxy]-, (1S,4R,5E,6R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Benzoic acid (1S,4R,6R)-4-benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enyl ester (588693-67-8) → (1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol (588693-71-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/ja0342998

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol (588693-71-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: i-Pr₂NEt; DMAP / 1,2-dichloro-ethane / 4 h / 60 °C

2.1: (+/-)-CSA; MeOH / 1 h / 20 °C

3.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C

4.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C

5.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C

6.1: NaBH₄ / methanol / 0.25 h / 20 °C

7.1: (+/-)-CSA / acetone / 0.67 h / 20 °C

7.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C

8.1: 99 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

With methanol; dmap; sodium tetrahydroborate; 10-camphorsufonic acid; magnesium ethylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; mercury(II) oxide; In pyridine; methanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetone;

DOI:10.1021/ja0342998

Reference yield:

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester (588693-55-4) → (1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol (588693-71-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: i-Pr₂NEt; DMAP / 1,2-dichloro-ethane / 4 h / 60 °C

2.1: (+/-)-CSA; MeOH / 1 h / 20 °C

3.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C

4.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C

5.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C

6.1: NaBH₄ / methanol / 0.25 h / 20 °C

7.1: (+/-)-CSA / acetone / 0.67 h / 20 °C

7.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C

8.1: 99 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

With methanol; dmap; sodium tetrahydroborate; 10-camphorsufonic acid; magnesium ethylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; mercury(II) oxide; In pyridine; methanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetone;

DOI:10.1021/ja0342998

upstream raw materials:

Benzoic acid (1S,4R,6R)-4-benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enyl ester

Benzyloxymethyl chloride

benzoic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

Benzoic acid (1S,5R,8S,8aR)-5-benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-1-hydroxymethyl-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester

Downstream raw materials:

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde

(1S,5R,6R,9R)-6-Benzyloxymethoxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-3-oxo-2-oxa-4-aza-bicyclo[3.3.1]non-7-ene-4-carboxylic acid tert-butyl ester

C₄₂H₅₁N₃O₁₈

Benzoic acid (1S,2R,3S,4R,5S,6R)-2-acetoxy-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester

Refernces