{(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate

Base Information

• Chemical Name: {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate
• CAS No.: 1290630-09-9
• Molecular Formula: C₅₇H₅₇ClO₁₁S₂
• Molecular Weight: 1017.66
• Mol file: 1290630-09-9.mol

Synonyms:{(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate

Chemical Property of {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate

There total 7 articles about {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate 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:

[(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)tetrahydropyran-2-yl]methanol (1290629-81-0) + p-toluenesulfonyl chloride (98-59-9) → {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate (1290630-09-9)

Guidance literature:

With pyridine; at 80 ℃; for 48h;

Reference yield:

[(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)tetrahydropyran-2-yl]methanol (1290629-81-0) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-ylmethyl ester (1290630-15-7) + {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate (1290630-09-9)

Guidance literature:

With pyridine; at 20 - 80 ℃;

Reference yield:

dapagliflozin (461432-26-8,1373321-04-0) → {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol bis-tosylate (1290630-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 18 h / 20 °C / Reflux

2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

2.2: 18 h / 20 °C

3.1: aluminum (III) chloride / dichloromethane; diethyl ether / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -70 °C

4.2: 0.25 h / 20 °C

4.3: 72 h / 20 °C

5.1: pyridine / 48 h / 80 °C

With pyridine; aluminum (III) chloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

[(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)tetrahydropyran-2-yl]methanol

p-toluenesulfonyl chloride

dapagliflozin

(2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

{(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-methyl-tetrahydro-pyran-2-yl}-methanol

(3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3,4,5-triol

Refernces

• 1、 -. "GLYCOSIDE DERIVATIVE AND USES THEREOF". Page/Page column 82. . Retrieved 2011/05/06.