Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside
• CAS No.: 87907-35-5
• Molecular Formula: C₂₂H₂₇NO₇
• Molecular Weight: 417.459
• DSSTox Substance ID: DTXSID501335407
• Mol file: 87907-35-5.mol

Synonyms:Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside;87907-35-5;DTXSID501335407;Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside min.

Chemical Property of Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 417.17875220
• Heavy Atom Count: 30
• Complexity: 508

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO)O)OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

Technology Process of Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside

There total 12 articles about Methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-alpha-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: 92.0%

methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-53-1) → methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5)

Guidance literature:

With methanol; acetyl chloride; at 24 ℃; for 2h;

DOI:10.1021/jo00039a044

Reference yield:

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1: CSA / tetrahydrofuran

2: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

3: aq. AcOH

With barium dihydroxide; camphor-10-sulfonic acid; acetic acid; barium(II) oxide; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Acetalization / 2: Alkylation / 3: Hydrolysis;

DOI:10.1016/S0960-894X(99)00550-8

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. Na₂CO₃

2: HCl

3: CSA / tetrahydrofuran

4: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

5: aq. AcOH

With hydrogenchloride; barium dihydroxide; camphor-10-sulfonic acid; sodium carbonate; acetic acid; barium(II) oxide; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Acylation / 2: Glycosidation / 3: Acetalization / 4: Alkylation / 5: Hydrolysis;

DOI:10.1016/S0960-894X(99)00550-8

upstream raw materials:

methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

(+)-D-glucosamine hydrochloride

Downstream raw materials:

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

methyl 3-O-benzyl-2-benzyloxycarbonylamino-6-O-chloroacetyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

Refernces

• 1、 Koshida, Shuhei,Suda, Yasuo,Sobel, Michael,Ormsby, Julie,Kusumoto, Shoichi. "Synthesis of heparin partial structures and their binding activities to platelets". . p. 3127 - 3132. Retrieved 2007/10/03.
• 2、 Coleman, Robert S.,Dong, Yong,Carpenter, Andrew J.. "A Convenient Preparation of Terminally Differentiated, Selectively Protected Six-Carbon Synthons from D-Glucosamine". . p. 3732 - 3735. Retrieved 2007/10/02.