Methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-prop-2-en-1-yl-beta-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-prop-2-en-1-yl-beta-D-glucopyranoside
• CAS No.: 116981-28-3
• Molecular Formula: C19H27NO6
• Molecular Weight: 365.42078
• DSSTox Substance ID: DTXSID80553882
• Nikkaji Number: J2.647.129J
• Wikidata: Q82434589
• Mol file: 116981-28-3.mol

Synonyms:116981-28-3;Methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-prop-2-en-1-yl-beta-D-glucopyranoside;N-[(2R,3R,4R,5S,6R)-5-Hydroxy-2-methoxy-6-(phenylmethoxymethyl)-4-prop-2-enoxyoxan-3-yl]acetamide;DTXSID80553882

Chemical Property of Methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-prop-2-en-1-yl-beta-D-glucopyranoside

Chemical Property:

• PSA: 89.74000
• LogP: 1.85160
• Storage Temp.: Room Temperature
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 365.18383758
• Heavy Atom Count: 26
• Complexity: 440

Purity/Quality:

95% ^*data from raw suppliers

Methyl2-(Acetylamino)-2-deoxy-6-O-benzyl-3-O-2-propen-1-yl-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC)COCC2=CC=CC=C2)O)OCC=C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC)COCC2=CC=CC=C2)O)OCC=C
• Uses: Used in the preparation of glycosides and oligosaccharides. Methyl 2-(AcetylaMino)-2-deoxy-6-O-(phenylMethyl)-3-O-2-propen-1-yl-β-D-glucopyranoside is used in the preparation of of glycosides and oligosaccharides.

Technology Process of Methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-prop-2-en-1-yl-beta-D-glucopyranoside

There total 2 articles about Methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-prop-2-en-1-yl-beta-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: 89.0%

methyl 2-acetamido-3-O-allyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (54968-13-7,67816-87-9,117064-55-8) → methyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside (116981-28-3)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

DOI:10.1016/0008-6215(88)85093-6

Reference yield:

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (87038-18-4) → methyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside (116981-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 2 h / Ambient temperature

2: 89 percent / sodium cyanoborohydride, molecular sieves 3 A; HCl / tetrahydrofuran; diethyl ether

With hydrogenchloride; barium dihydroxide; 3 A molecular sieve; sodium cyanoborohydride; barium(II) oxide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(88)85093-6

Reference yield: 77.0%

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide (84439-23-6) + methyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside (116981-28-3) → methyl 2-acetamido-3-O-allyl-4-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (116981-33-0)

Guidance literature:

With calcium sulfate; 4 A molecular sieve; mercury(II) cyanide; In nitromethane; toluene; 1.) 1.5 h; 2.) 3 h;

DOI:10.1016/0008-6215(88)85093-6

upstream raw materials:

methyl 2-acetamido-3-O-allyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

methyl 2-acetamido-3-O-allyl-4-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2,3-dideoxy-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-xylo-hexopyranoside

methyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-6-O-benzyl-2,3-dideoxy-β-D-xylo-hexopyranoside

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