2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol

Base Information

• Chemical Name: 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol
• CAS No.: 202460-02-4
• Molecular Formula: C₃₅H₄₇N₃O₆Si
• Molecular Weight: 633.86

Synonyms:2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol

Chemical Property of 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol

Chemical Property:

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Technology Process of 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol

There total 4 articles about 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 5-azido-5-deoxy-4-O-(4-methoxybenzyl)-1,2-O-(1-ethylpropylidene)-L-mannitol (202460-01-3) → 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol (202460-02-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 10.2h;

DOI:10.1246/bcsj.71.259

Reference yield:

pentan-3-one (96-22-0) → 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol (202460-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.48 g / p-toluenesulfonic acid monohydrate / 5 h / 20 °C

2: 100 percent / imidazole / dimethylformamide / 10.2 h / 0 - 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: Cyclization / 2: silylation;

DOI:10.1246/bcsj.71.259

Reference yield:

(2S,3S,4S,5S)-5-Azido-4-(4-methoxy-benzyloxy)-hexane-1,2,3,6-tetraol → 2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol (202460-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.48 g / p-toluenesulfonic acid monohydrate / 5 h / 20 °C

2: 100 percent / imidazole / dimethylformamide / 10.2 h / 0 - 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; 1: Cyclization / 2: silylation;

DOI:10.1246/bcsj.71.259

upstream raw materials:

tert-butylchlorodiphenylsilane

5-azido-5-deoxy-4-O-(4-methoxybenzyl)-1,2-O-(1-ethylpropylidene)-L-mannitol

pentan-3-one

2-azido-2-deoxy-4,5-O-isopropylidene-3-O-(4-methoxybenzyl)-L-mannitol

Downstream raw materials:

2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-4-O-methanesulfonyl-3-O-(4-methoxybenzyl)-5,6-O-(1-ethylpropylidene)-L-mannitol

2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-3-O-(4-methoxybenzyl)-D-4,5-anhydroribitol

2-azido-1-O-(t-butyldiphenylsilyl)-2-deoxy-4-O-methanesulfonyl-3-O-(4-methoxybenzyl)-L-mannitol

(2S,3S,4R)-2-(t-butoxycarbonyl)amino-1-(t-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-4-hexadecanol

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