Methyl2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-alpha-D-glucopyranoside
• CAS No.: 4704-15-8
• Molecular Formula: C15H21NO7
• Molecular Weight: 327.334
• Mol file: 4704-15-8.mol

Synonyms:2-benzyl-3-methoxy-3-oxopropanoic acid;Propanedioic acid,(phenylmethyl)-,monomethyl ester;Benzylmalonsaeuremonomethylester;methyl 2-benzylmalonate;

Chemical Property of Methyl2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-alpha-D-glucopyranoside

Chemical Property:

• PSA: 120.97000
• LogP: -0.42880

Purity/Quality:

98%min ^*data from raw suppliers

MethylN-Benzyloxycarbonyl-α-D-glucosaminide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl N-Benzyloxycarbonyl-α-D-glucosaminide is the derivative of D-Glucosamine Hydrochloride (G514950), which is used to prepare medical agent for treating vertigo. Found in chitin, in mucoproteins, and in mucopolysaccharides. Antiarthritic. Recent studies show that its chondroprotective activity is related to its antiapoptic properties.

Technology Process of Methyl2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-alpha-D-glucopyranoside

There total 10 articles about Methyl2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-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: 75.0%

methanol (67-56-1) + 2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8)

Guidance literature:

With Amberlite IR-120(H⁺); for 24h; Heating;

DOI:10.1021/jo00210a030

Reference yield: 21.0%

methanol (67-56-1) + 2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → benzyl ((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3-yl)carbamate (4704-17-0) + ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8)

Guidance literature:

With hydrogenchloride; In water; at 70 ℃; for 1h;

DOI:10.1039/c5ob00211g

Reference yield:

methanol (67-56-1) + benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (77059-32-6) → ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8)

Guidance literature:

With hydrogenchloride; for 7h; Heating;

DOI:10.1081/CAR-120004331

upstream raw materials:

methanol

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

2-benzyloxycarbonylamino-2-deoxy-D-glucose

benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

Downstream raw materials:

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

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

[(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

methyl 3,4-di-O-acetyl-2-(benzyloxycarbonylamino)-2-deoxy-6-O-trityl-α-D-glucopyranoside