tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 132125-23-6
• Molecular Formula: C₆₉H₈₅N₃O₁₄Si
• Molecular Weight: 1208.53
• Mol file: 132125-23-6.mol

Synonyms:tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 6 articles about tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-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: 89.0%

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (120703-59-5) + tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (132100-99-3) → tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (132125-23-6)

Guidance literature:

zinc chloride diethyl ether; In dichloromethane; for 0.5h;

Reference yield:

benzyl bromide (100-39-0) → tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (132125-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / sodium hydride / dimethylformamide / 5 h / 0 °C

2: 1) H₂, 2) mercury(II) oxide, mercury(II) chloride / 1) (1,5-cyclooctadiene)bis-(methyldiphenylphosphine)iridium hexafluorophosphate / 1) THF, 3-4 h, 2) acetone/water, 1 h

3: 89 percent / ZnCl₂*Et₂O / CH₂Cl₂ / 0.5 h

With hydrogen; sodium hydride; mercury dichloride; mercury(II) oxide; zinc chloride diethyl ether; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

tert-butyldimethylsilyl 2-azido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (121865-28-9) → tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (132125-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / NaH / dimethylformamide / 72 h / -10 °C

2: 92 percent / iron(III) chloride / 0.5 h / Heating

3: 83 percent / sodium hydride / dimethylformamide / 5 h / 0 °C

4: 1) H₂, 2) mercury(II) oxide, mercury(II) chloride / 1) (1,5-cyclooctadiene)bis-(methyldiphenylphosphine)iridium hexafluorophosphate / 1) THF, 3-4 h, 2) acetone/water, 1 h

5: 89 percent / ZnCl₂*Et₂O / CH₂Cl₂ / 0.5 h

With hydrogen; iron(III) chloride; sodium hydride; mercury dichloride; mercury(II) oxide; zinc chloride diethyl ether; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate

tert-Butyldimethylsilyl O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

benzyl bromide

tert-butyldimethylsilyl 2-azido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside

Downstream raw materials:

O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl Trichloroacetimidate

O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-α-D-glucopyranosyl Trichloroacetimidate

2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-desoxy-β-D-glucopyranoside

2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-desoxy-α-D-glucopyranoside