methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate

Base Information

• Chemical Name: methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate
• CAS No.: 811867-68-2
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373
• Mol file: 811867-68-2.mol

Synonyms:methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate

Chemical Property of methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate

There total 7 articles about methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate 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:

(2R,3R)-1,4-diiodo-2,3-dimethoxybutane (6963-02-6,58313-57-8,58313-64-7,58342-58-8) → methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate (811867-68-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 53 percent / t-BuOK / dimethylsulfoxide / 48 h

2.1: NaOH / H₂O; methanol / 5 h / 0 °C

3.1: diphenylphosphoryl azide; triethylamine / benzene / 1 h / Heating

3.2: 712 mg / benzene / 6 h / Heating

With sodium hydroxide; diphenylphosphoranyl azide; potassium tert-butylate; triethylamine; In methanol; water; dimethyl sulfoxide; benzene; 3.1: Curtius rearrangement;

DOI:10.1002/anie.200460420

Reference yield:

methyl (3S,4S)-3,4-dimethoxy-1-(methoxycarbonyl)cyclopentanecarboxylate (811867-67-1) → methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate (811867-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOH / H₂O; methanol / 5 h / 0 °C

2.1: diphenylphosphoryl azide; triethylamine / benzene / 1 h / Heating

2.2: 712 mg / benzene / 6 h / Heating

With sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In methanol; water; benzene; 2.1: Curtius rearrangement;

DOI:10.1002/anie.200460420

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) + (3S,4S)-3,4-Dimethoxy-cyclopentane-1,1-dicarboxylic acid methyl ester (811867-76-2) → methyl (3S,4S)-1-benzyloxycarbonylamino-3,4-(dimethoxy)cyclopentanecarboxylate (811867-68-2)

Guidance literature:

(3S,4S)-3,4-Dimethoxy-cyclopentane-1,1-dicarboxylic acid methyl ester; With diphenylphosphoranyl azide; triethylamine; In benzene; for 1h; Heating;

benzyl alcohol; In benzene; for 6h; Heating;

DOI:10.1002/anie.200460420

upstream raw materials:

benzyl alcohol

(3S,4S)-3,4-Dimethoxy-cyclopentane-1,1-dicarboxylic acid methyl ester

(2R,3R)-1,4-diiodo-2,3-dimethoxybutane

methyl (3S,4S)-3,4-dimethoxy-1-(methoxycarbonyl)cyclopentanecarboxylate

Downstream raw materials:

Cbz-[(S,S)-Ac₅c(dOM)]6-OMe

methyl (3S,4S)-3,4-dimethoxy-1-{[(3S,4S)-3,4-dimethoxy-1-{[(3S,4S)-3,4-dimethoxy-1-{[(3S,4S)-3,4-dimethoxy-1-(benzyloxycarbonylamino)cyclopentyl]carbonylamino}cyclopentyl]carbonylamino}cyclopentyl]carbonylamino}cyclopentanecarboxylate

(3S,4S)-3,4-dimethoxy-1-{[(3S,4S)-3,4-dimethoxy-1-(benzyloxycarbonylamino)-cyclopentyl]carbonylamino}cyclopentanecarboxylic acid

methyl (3S,4S)-3,4-dimethoxy-1-{[(3S,4S)-3,4-dimethoxy-1-(benzyloxycarbonylamino)-cyclopentyl]carbonylamino}cyclopentanecarboxylate