1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside

Base Information

• Chemical Name: 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside
• CAS No.: 1421868-57-6
• Molecular Formula: C₅₆H₆₄O₁₀Si
• Molecular Weight: 925.204
• Mol file: 1421868-57-6.mol

Synonyms:1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside

Chemical Property of 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside

There total 6 articles about 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-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:

2-O-(4-methoxybenzyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol (544686-85-3) + 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl iodide (441017-58-9) → 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside (1421868-57-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at 20 ℃; for 144h; diastereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/jo302508e

Reference yield:

1,6-di-O-(tert-butyldiphenylsilyl)-2,5-di-O-(4-methoxybenzyl)-D-mannitol (1421868-56-5) → 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside (1421868-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate / water; tetrahydrofuran / 3 h / 20 °C

2: sodium tetrahydroborate / water; ethanol / 2 h / 0 °C

3: tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 144 h / 20 °C / Molecular sieve; Inert atmosphere

With sodium tetrahydroborate; sodium periodate; tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/jo302508e

Reference yield:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5) → 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside (1421868-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl iodide / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 144 h / 20 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl iodide; tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

DOI:10.1021/jo302508e

upstream raw materials:

1,6-di-O-(tert-butyldiphenylsilyl)-2,5-di-O-(4-methoxybenzyl)-D-mannitol

(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal

2-O-(4-methoxybenzyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl iodide

Downstream raw materials:

1-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-sn-glyceride

benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

benzyl (2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

benzyl (1-O-stearyl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate