N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester
• CAS No.: 144923-62-6
• Molecular Formula: C₃₁H₄₂N₂O₁₄
• Molecular Weight: 666.679
• Mol file: 144923-62-6.mol

Synonyms:N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester

Chemical Property of N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester

There total 3 articles about N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine 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: 45.0%

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7) + ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranoside (863997-29-9) → N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester (144923-62-6)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)79082-4

Reference yield: 45.0%

3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide (104655-87-0) + 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7) → N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester (144923-62-6)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1016/S0957-4166(00)80230-X

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-serine tert-butyl ester (144923-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dicyclohexylcarbodiimide, copper-(I)-chloride / 1.) 5 d, 2.) dichloromethane

2: 45 percent / molecular sieves 4A, mercuric cyanide / CH₂Cl₂ / 4 h / Ambient temperature

With 4 A molecular sieve; mercury(II) cyanide; dicyclohexyl-carbodiimide; copper(l) chloride; In dichloromethane;

DOI:10.1016/S0957-4166(00)80230-X

upstream raw materials:

3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester

ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-1-thio-β-D-glucopyranoside

N-(benzyloxycarbonyl)-L-serine