4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester
• CAS No.: 236388-69-5
• Molecular Formula: C₅₀H₅₆N₂O₁₁
• Molecular Weight: 861.001
• Mol file: 236388-69-5.mol

Synonyms:4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester

Chemical Property of 4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester

There total 1 articles about 4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-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: 76.0%

4-nitro-benzoyl chloride (122-04-3) + [1-Hydroxymethyl-3-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester → 4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester (236388-69-5) + 4-Nitro-benzoic acid (R)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester

Guidance literature:

In pyridine; for 14h; Ambient temperature;

DOI:10.1021/jo990398l

Reference yield: 90.0%

4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester (236388-69-5) → 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol (144542-40-5)

Guidance literature:

With sodium methylate; In methanol; for 15h; Ambient temperature;

DOI:10.1021/jo990398l

Reference yield:

4-Nitro-benzoic acid (S)-2-tert-butoxycarbonylamino-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyl ester (236388-69-5) → 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitose (236388-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / MeONa / methanol / 15 h / Ambient temperature

2: 90 percent / (COCl)2, DMSO, DIPEA / CH₂Cl₂ / -78 - 0 °C

With oxalyl dichloride; sodium methylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/jo990398l

upstream raw materials:

4-nitro-benzoyl chloride

Downstream raw materials:

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol

5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitose

(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

(3'S,4'R)-3'-aminononadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside