(2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid

Base Information

• Chemical Name: (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid
• CAS No.: 182550-35-2
• Molecular Formula: C₃₁H₃₇NO₇
• Molecular Weight: 535.637

Synonyms:(2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid

Chemical Property of (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid

Chemical Property:

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Technology Process of (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid

There total 4 articles about (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid 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:

5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol (182550-30-7) → (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid (182550-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) (COCl)2, DMSO, Et₃N, 2.) Br₂, NaHCO₃ / 1.) CH₂Cl₂, -78 deg C, 2.) H₂O

2: 70 percent / PPh₃ / H₂O; benzene

3: DMAP

4: 1 M aq. NaOH

With dmap; sodium hydroxide; oxalyl dichloride; bromine; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In water; benzene;

DOI:10.1016/0040-4039(96)01277-4

Reference yield:

(2S,3R,4R)-5-Azido-2,3,4-tris-benzyloxy-pentanoic acid methyl ester (182550-31-8) → (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid (182550-35-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / PPh₃ / H₂O; benzene

2: DMAP

3: 1 M aq. NaOH

With dmap; sodium hydroxide; triphenylphosphine; In water; benzene;

DOI:10.1016/0040-4039(96)01277-4

Reference yield:

(3S,4R,5R)-tert-butyl 3,4,5-tris(benzyloxy)-2-oxopiperidine-1-carboxylate → (2S,3R,4R)-2,3,4-Tris-benzyloxy-5-tert-butoxycarbonylamino-pentanoic acid (182550-35-2)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/0040-4039(96)01277-4

upstream raw materials:

(3S,4R,5R)-3,4,5-tri(benzyloxy)piperidin-2-one

5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol

(2S,3R,4R)-5-Azido-2,3,4-tris-benzyloxy-pentanoic acid methyl ester

Downstream raw materials:

[(2R,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester

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