Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-D-glucopyranoside
• CAS No.: 85193-92-6
• Molecular Formula: C23H29 N O6
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID50458572
• Nikkaji Number: J1.355.155C
• Wikidata: Q82281979
• Mol file: 85193-92-6.mol

Synonyms:85193-92-6;Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-D-glucopyranoside;N-[(2S,3R,4R,5S,6R)-5-hydroxy-2-methoxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide;SCHEMBL10525210;DTXSID50458572;W-203939;1-O-Methyl-N-acetyl-3-O,6-O-dibenzyl-alpha-D-glucosamine;Benzyl-2-acetamido-2-deoxy-3,6-di-O-benzyl-alpha-D-glucopyranoside;Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside;Methyl 2-acetamido-3,6-di-O-benzyl-2-Deoxy-alpha-d-glucopyranoside?

Chemical Property of Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-D-glucopyranoside

Chemical Property:

• PSA: 86.25000
• LogP: 2.41640
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 415.19948764
• Heavy Atom Count: 30
• Complexity: 506

Purity/Quality:

95% ^*data from raw suppliers

Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-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)OCC3=CC=CC=C3
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OC)COCC2=CC=CC=C2)O)OCC3=CC=CC=C3

Technology Process of Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-D-glucopyranoside

There total 7 articles about Methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-a-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: 81.2%

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (69892-42-8) → methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (85193-92-6)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

DOI:10.1016/0008-6215(83)88241-X

Reference yield: 74.0%

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (144789-65-1) → methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (85193-92-6)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1039/b105872j

Reference yield: 39.0%

methyl N,N-diacetyl-2-amino-2-deoxy-4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (354986-43-9) → methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (85193-92-6) + methyl N,N-diacetyl-2-amino-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/ja010086b

upstream raw materials:

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl N,N-diacetyl-2-amino-2-deoxy-4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

benzyl bromide

Downstream raw materials:

methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside

methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-mesyl-α-D-glucopyranoside

methyl 2-acetamido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

methyl [2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-4-O-(1-naphthylmethyl)-β-D-glucopyranosyl]-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside)

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