[((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Base Information

• Chemical Name: [((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester
• CAS No.: 315229-39-1
• Molecular Formula: C₂₂H₃₄N₂O₁₀
• Molecular Weight: 486.519

Synonyms:[((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Chemical Property of [((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Chemical Property:

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Technology Process of [((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

There total 2 articles about [((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + ((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester (315229-38-0) → [((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester (315229-39-1)

Guidance literature:

In methanol; at 25 ℃;

DOI:10.1016/S0040-4020(00)00787-0

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → [((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester (315229-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / NaBH₃CN / methanol / 24 h / Heating

2: 96 percent / methanol / 25 °C

With sodium cyanoborohydride; In methanol; 1: Condensation / 2: Acylation;

DOI:10.1016/S0040-4020(00)00787-0

Reference yield:

[((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester (315229-39-1) → [(2-benzyloxycarbonylamino-3-oxo-propyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Guidance literature:

With sodium periodate; In dichloromethane; water; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00787-0

upstream raw materials:

di-tert-butyl dicarbonate

((2S,3R,4S,5R)-2-Benzyloxycarbonylamino-3,4,5,6-tetrahydroxy-hexylamino)-acetic acid methyl ester

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

methyl [(2S)-2-(benzyloxycarbonylamino)-3-hydroxypropyl(tert-butoxycarbonyl)amino]acetate

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