Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside
• CAS No.: 60076-41-7
• Molecular Formula: C22H25NO7
• Molecular Weight: 415.443
• Mol file: 60076-41-7.mol

Synonyms:Methyl 4,6-O-benzylidene-N-Cbz-alpha-D-glucosaminide;Methyl 4,6-O-benzylidene-N-Cbz-2-deoxy-α-D-glucopyranosaminide;Methyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside;Methyl 4,6-O-benzylidene-2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside min. 99%;Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-α-D-glucopyranoside;α-D-Glucopyranoside, methyl 2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-;Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

Chemical Property of Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Methyl4,6-O-Benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Methyl 4,6-O-Benzylidene-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside can be used as reagent/reactant in synthetic preparation of heparin partial structures and their binding activities to human platelets.

Technology Process of Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside

There total 8 articles about Methyl-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-4,6-O-(phenylmethylene)-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: 87.0%

benzaldehyde (100-52-7) + ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (60076-41-7)

Guidance literature:

With formic acid; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol2027703

Reference yield: 73.0%

benzaldehyde dimethyl acetal (1125-88-8) + ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (60076-41-7)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 90 ℃;

DOI:10.1021/jo00039a044

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (60076-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. Na₂CO₃

2: HCl

3: CSA / tetrahydrofuran

With hydrogenchloride; camphor-10-sulfonic acid; sodium carbonate; In tetrahydrofuran; 1: Acylation / 2: Glycosidation / 3: Acetalization;

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

upstream raw materials:

benzaldehyde dimethyl acetal

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

(+)-D-glucosamine hydrochloride

Downstream raw materials:

methyl 3-O-acetyl-2-benzyloxycarbonylamino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

methyl-[O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside]

methyl-[O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-O³-methanesulfonyl-2-deoxy-α-D-glucopyranoside]

methyl-[O⁴,O⁶-((Ξ)-benzylidene)-2-benzyloxycarbonylamino-O³-(toluene-4-sulfonyl)-2-deoxy-α-D-glucopyranoside]