(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester

Base Information

• Chemical Name: (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester
• CAS No.: 161105-41-5
• Molecular Formula: C₂₄H₃₆N₂O₁₀
• Molecular Weight: 512.557

Synonyms:(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester

Chemical Property of (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester

Chemical Property:

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Technology Process of (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester

There total 4 articles about (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl 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: 93.0%

(2S,3R)-2-Benzyloxycarbonylamino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyric acid tert-butyl ester → (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester (161105-41-5)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(00)78495-4

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide (67673-39-6) → (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester (161105-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent

2: 70 percent

3: 93 percent / sodium methoxide / methanol

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(00)78495-4

Reference yield:

tert-butyl (2S,3R)-2-(benzyloxycarbonyl)amino-3-hydroxybutanoate (72289-51-1) → (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxycarbonylamino-butyric acid tert-butyl ester (161105-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent

2: 70 percent

3: 93 percent / sodium methoxide / methanol

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(00)78495-4

upstream raw materials:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide

tert-butyl (2S,3R)-2-(benzyloxycarbonyl)amino-3-hydroxybutanoate

Downstream raw materials:

C₄₄H₆₃N₃O₂₂

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