Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 129729-15-3
• Molecular Formula: C₆₂H₇₀O₁₄Si
• Molecular Weight: 1067.31

Synonyms:

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl 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: 6.7%

tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside (129729-18-6) + acetyl chloride (75-36-5) → tert-butyldiphenylsilyl O-(6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (120654-52-6) + Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester (129729-15-3)

Guidance literature:

With pyridine; at 0 - 10 ℃; for 3h;

DOI:10.1016/0008-6215(90)84203-7

Reference yield:

(4aR,7R,8S,8aS)-7,8-Bis-benzyloxy-6-fluoro-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine (119479-70-8) → Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester (129729-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 8.9 percent / Sn(OTf)2, molecular sieves 4 Angstroem / diethyl ether

2: 6.7 percent / pyridine / 3 h / 0 - 10 °C

With pyridine; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether;

DOI:10.1016/0008-6215(90)84203-7

Reference yield:

tert-butyldiphenylsilyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (113765-21-2) → Acetic acid (2R,3S,4S,5R,6S)-3-((2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester (129729-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 8.9 percent / Sn(OTf)2, molecular sieves 4 Angstroem / diethyl ether

2: 6.7 percent / pyridine / 3 h / 0 - 10 °C

With pyridine; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether;

DOI:10.1016/0008-6215(90)84203-7

upstream raw materials:

tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside

acetyl chloride

(4aR,7R,8S,8aS)-7,8-Bis-benzyloxy-6-fluoro-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

tert-butyldiphenylsilyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside

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