Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate

Base Information

• Chemical Name: Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate
• CAS No.: 934591-79-4
• Molecular Formula: C17H21NO8S
• Molecular Weight: 399.42

Synonyms:Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate;(3aR,4R,6R,7aS)-Hexahydro-2-oxo-6-(phenylthio)-4-[(1R,2R)-1,2,3-trihydroxypropyl]-4H-pyrano[3,4-d]oxazole-6-carboxylic acid methyl ester;-D-galacto-2-nonulopyranosylonate;Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-&beta

Chemical Property of Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate

Chemical Property:

• Boiling Point: 734.5±60.0 °C(Predicted)
• PKA: 10.38±0.60(Predicted)
• PSA: 159.85000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: -0.04320

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-b-D-galacto-2-nonulopyranosylonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate

There total 2 articles about Methyl 5-N,4-O-Carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate 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: 78.0%

4-Nitrophenyl chloroformate (7693-46-1) + methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate (118977-25-6) → methyl (phenyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate (934591-79-4)

Guidance literature:

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate; With methanesulfonic acid; In methanol; for 24h; Heating;

4-Nitrophenyl chloroformate; With sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃; for 3h;

DOI:10.1021/jo062431r

Reference yield: 74.0%

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate (118977-25-6,118977-26-7) → methyl (phenyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate (934591-79-4)

Guidance literature:

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate; With methanesulfonic acid; In methanol; for 24h; Inert atmosphere; Reflux;

With 4-Nitrophenyl chloroformate; In water; acetonitrile; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.7b03117

Reference yield: 62.0%

methyl (phenyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate (934591-79-4) + benzaldehyde dimethyl acetal (1125-88-8) → methyl (phenyl 5-amino-8,9-O-benzylidene-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (898224-35-6)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/acs.orglett.0c02692

upstream raw materials:

4-Nitrophenyl chloroformate

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate

Downstream raw materials:

methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside

methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galactonon-2-ulopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ylopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 5-acetamido-3,5-dideoxy-D-glycero-β-D-galactonon-2-ulopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

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