Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside
• CAS No.: 207272-72-8
• Molecular Formula: C₆₉H₇₃NO₁₀
• Molecular Weight: 1076.34
• Mol file: 207272-72-8.mol

Synonyms:Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside

Chemical Property of Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside

There total 10 articles about Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside 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: 61.0%

((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-[(2S,3R,4R,5S,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohex-(E)-ylidene]-amine (207272-71-7) → Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside (207272-72-8)

Guidance literature:

With sodium cyanoborohydride; In N,N-dimethyl-formamide; 1.) 20 deg C, 70 h, 2.) 100 deg C, 1 h;

DOI:10.1039/a800279g

Reference yield: 61.0%

Methyl 3-amino-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranoside (207272-64-8) + (+)-2,3,5/4,6-Pentabenzyloxycyclohexanone (207296-28-4) → Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside (207272-72-8)

Guidance literature:

Methyl 3-amino-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranoside; (+)-2,3,5/4,6-Pentabenzyloxycyclohexanone; With 4 A molecular sieve; In benzene; at 20 ℃; for 70h;

With sodium cyanoborohydride; In N,N-dimethyl-formamide; at 20 - 100 ℃;

DOI:10.1016/j.carres.2009.09.008

Reference yield:

(+)-2,3,5/4,6-Pentabenzyloxycyclohexanone (207296-28-4) → Methyl 2,4,6-tri-O-benzyl-3-[(1S,2S,3S,4R,5R,6S)-2,3,4,5,6-pentabenzyloxycyclohexylamino]-3-deoxy-α-D-glucopyranoside (207272-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves / benzene / 70 h / 20 °C

2: Na(CN)BH₃ / dimethylformamide / 72 h / 20 - 100 °C

With 4 A molecular sieve; sodium cyanoborohydride; In N,N-dimethyl-formamide; benzene; 1: Condensation / 2: Reduction;

DOI:10.1039/a902826i

upstream raw materials:

((2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-[(2S,3R,4R,5S,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohex-(E)-ylidene]-amine

methyl-3-azido-3-deoxy-α-D-glucopyranoside

(+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol

benzyl bromide