(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Base Information

• Chemical Name: (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
• CAS No.: 1242144-15-5
• Molecular Formula: C₅₄H₈₂O₉Si
• Molecular Weight: 903.325
• Mol file: 1242144-15-5.mol

Synonyms:(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Chemical Property of (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

There total 4 articles about (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-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: 46.0%

O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate (1201598-10-8) + (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol (1215176-80-9) → (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (1242144-15-5) + (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1215176-83-2)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 2.5h; Molecular sieve;

DOI:10.1016/j.carres.2010.05.003

Reference yield:

(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol (1215176-80-9) + O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (303752-87-6) → (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (1242144-15-5) + (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1215176-83-2)

Guidance literature:

(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol; O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieves 4 ?;

With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 2.5h;

Reference yield:

(2S,3S,4R,5EZ)-1-tert-butyldimethylsilyloxy-3,4-O-isopropylidene-5-octadecen-2-ol (1215176-72-9) → (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (1242144-15-5) + (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1215176-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / palladium hydroxide on carbon / ethyl acetate / 1 h / 20 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

3.1: pyridine; pyridine hydrofluoride / tetrahydrofuran / 4 h / 0 - 20 °C

4.1: dichloromethane / 0.5 h / 20 °C / Molecular sieves 4 ?

4.2: 2.5 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; pyridine hydrofluoride; hydrogen; palladium hydroxide on carbon; In tetrahydrofuran; dichloromethane; ethyl acetate;

upstream raw materials:

O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate

(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol

(2S,3S,4R,5EZ)-1-tert-butyldimethylsilyloxy-3,4-O-isopropylidene-5-octadecen-2-ol

(2S)-2-(tert-butyldimethylsilyloxy)-1-((4S,5S)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethanol