Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

Base Information

• Chemical Name: Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester
• CAS No.: 270928-23-9
• Molecular Formula: C₅₁H₅₀O₁₅
• Molecular Weight: 902.949
• Mol file: 270928-23-9.mol

Synonyms:Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

Chemical Property of Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

There total 3 articles about Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester 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: 74.0%

((2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-trimethyl-silane + Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-ethanesulfinyl-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester → Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester (270928-23-9)

Guidance literature:

With trifluoromethanesulfonic acid anhydride; In dichloromethane; at -78 - -40 ℃; for 5h;

DOI:10.1021/ol005732a

Reference yield:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9) → Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester (270928-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

2: m-CPBA / CH₂Cl₂ / 0.08 h / -78 °C

3: 74 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / 5 h / -78 - -40 °C

With boron trifluoride diethyl etherate; trifluoromethanesulfonic acid anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1: Substitution / 2: Oxidation / 3: glycosilation;

DOI:10.1021/ol005732a

Reference yield:

Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-ethylsulfanyl-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester (270071-30-2) → Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester (270928-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: m-CPBA / CH₂Cl₂ / 0.08 h / -78 °C

2: 74 percent / trifluoromethanesulfonic anhydride / CH₂Cl₂ / 5 h / -78 - -40 °C

With trifluoromethanesulfonic acid anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1: Oxidation / 2: glycosilation;

DOI:10.1021/ol005732a

upstream raw materials:

4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-ethylsulfanyl-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester

Downstream raw materials:

etoposide

Refernces