methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside
• CAS No.: 484000-91-1
• Molecular Formula: C₂₄H₃₉BrO₇Si
• Molecular Weight: 547.559

Synonyms:methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside

Chemical Property of methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside

Chemical Property:

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Technology Process of methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside

There total 3 articles about methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside 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: 80.0%

2-bromo-5-methoxybenzyl bromide (19614-12-1) + methyl 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (220115-72-0) → methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside (484000-91-1)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200700762

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside (484000-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

2: TBAB; 50 percentNaOH / CH₂Cl₂ / 8 h / 25 °C

With 1H-imidazole; sodium hydroxide; tetrabutylammomium bromide; In dichloromethane;

DOI:10.1016/S0040-4039(02)01252-2

Reference yield:

methyl 2,3-O-isopropylidene-α-D-mannopyranoside (63167-69-1) → methyl 6-O-(tert-butyldimethylsilyl)-4-O-(2-bromo-5-methoxybenzyl)-2,3-O-isopropylidene-α-D-mannopyranoside (484000-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

2: TBAB; 50 percentNaOH / CH₂Cl₂ / 8 h / 25 °C

With 1H-imidazole; sodium hydroxide; tetrabutylammomium bromide; In dichloromethane;

DOI:10.1016/S0040-4039(02)01252-2

upstream raw materials:

2-bromo-5-methoxybenzyl bromide

methyl 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

tert-butyldimethylsilyl chloride

methyl 2,3-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

(3aS,4S,6R,7R,7aS)-[7-(2-bromo-5-methoxybenzyloxy)-4-methoxy-2,2-dimethyltetrahydro-2H,4H-[1,3]dioxolo[4,5-c]pyran-6-yl]methanol

(3aS,4S,6S,7S,7aS)-7-(2-Bromo-5-methoxy-benzyloxy)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

(3aS,4S,6R,7R,7aS)-7-(2-Bromo-5-methoxy-benzyloxy)-4-methoxy-2,2-dimethyl-6-vinyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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