methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside
• CAS No.: 83532-15-4
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373
• Mol file: 83532-15-4.mol

Synonyms:methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside

Chemical Property of methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside

There total 8 articles about methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside 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: 53.0%

methyl 3-(benzyloxycarbonyl)amino-4-(E)-methoxymethylene-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside (138456-68-5) → methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside (83532-15-4)

Guidance literature:

With oxygen; copper(l) chloride; palladium dichloride; In N,N-dimethyl-formamide; at 70 ℃; for 1h; also oxidation with pyridinium chlorochromate in CH₂Cl₂, r.t., 24 h;

DOI:10.1248/cpb.39.2201

Reference yield: 30.0%

{(2R,4R,6S)-6-Methoxy-3-[1-methoxy-meth-(Z)-ylidene]-2-methyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester (83532-14-3) → methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside (83532-15-4)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; Ambient temperature;

DOI:10.1248/cpb.30.1929

Reference yield:

methyl 3-(N-benzyloxycarbonylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside (83532-10-9) → methyl 3-(benzyloxycarbonyl)amino-4-methoxycarbonyl-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside (83532-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / dimethylsulfoxide-trifluoracetic anhydride / CH₂Cl₂ / -65 °C

2: 1.) Li, 2.) potassium hydride / 1.) THF, -65 deg C; 2.) THF, DMF, 0 deg C

3: 30 percent / pyridinium chlorochromate / CH₂Cl₂ / Ambient temperature

With lithium; potassium hydride; dimethyl sulfoxide; pyridinium chlorochromate; trifluoroacetic anhydride; In dichloromethane;

DOI:10.1248/cpb.30.1929

upstream raw materials:

methyl 3-(benzyloxycarbonyl)amino-4-(E)-methoxymethylene-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranoside

{(2R,4R,6S)-6-Methoxy-3-[1-methoxy-meth-(Z)-ylidene]-2-methyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside

methyl 3-(N-benzyloxycarbonylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside

Downstream raw materials:

p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one

(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone