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

Base Information

• Chemical Name: tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside
• CAS No.: 129729-18-6
• Molecular Formula: C₅₈H₆₆O₁₂Si
• Molecular Weight: 983.24
• Mol file: 129729-18-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranoside 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: 91.2%

tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (113765-30-3) → 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)

Guidance literature:

With acetic acid; In tetrahydrofuran; for 48h; Ambient temperature;

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

Reference yield: 61.8%

(4aR,7R,8S,8aS)-7,8-Bis-benzyloxy-6-fluoro-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine (119479-70-8) + tert-butyldiphenylsilyl 6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (113765-21-2) → 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) + tert-butyldiphenylsilyl O-(2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-galactopyranosyl)-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside (113765-30-3)

Guidance literature:

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

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) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 61.8 percent / Sn(OTf)2, molecular sieves 4 Angstroem / diethyl ether

2: 91.2 percent / aq. 80percent AcOH / tetrahydrofuran / 48 h / Ambient temperature

With tin(II) trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; In tetrahydrofuran; diethyl ether;

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

upstream raw materials:

(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

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

Downstream raw materials:

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

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