tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside
• CAS No.: 142657-27-0
• Molecular Formula: C₃₇H₅₀O₁₄Si
• Molecular Weight: 746.881
• Mol file: 142657-27-0.mol

Synonyms:tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

There total 4 articles about tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside 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: 19.0%

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3) + tert-butyldimethylsilyl 6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside (142657-26-9) → tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside (142657-27-0) + tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->4)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside (142657-28-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 1h; Ambient temperature;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside (142657-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) RT, 3 h

2: 51 percent / molecular sieves 4 Angstroem, TMSOTF / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine; In dichloromethane;

Reference yield:

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (37776-15-1) → tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside (142657-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / 80percent aq. HOAc / 2.5 h / 110 °C

2: 62 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) RT, 3 h

3: 51 percent / molecular sieves 4 Angstroem, TMSOTF / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; triethylamine; In dichloromethane;

upstream raw materials:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate

tert-butyldimethylsilyl 6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

tert-butyldimethylsilyl chloride

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α/β-D-glucopyranoside

O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-(1->4)-<(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)>-6-O-benzoyl-3-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

tert-butyldimethylsilyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-6-O-benzoyl-3-O-benzyl-4-O-trichloroacetyl-β-D-glucopyranoside