(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester
CAS No.:151074-57-6
Molecular Formula:C₁₄H₁₇NO₅
Molecular Weight:279.293
Hs Code.:

Synonyms:(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

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Chemical Property of (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

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Technology Process of (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

There total 9 articles about (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester 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%

: 175694-63-0
methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate

: 151074-57-6
(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;
DOI:10.1016/0957-4166(96)00038-9

Reference yield: 83.0%

: 114498-10-1
(1S,2R)-1-Amino-2-hydroxymethyl-cyclopropanecarboxylic acid methyl ester

: 501-53-1,94274-21-2
benzyl chloroformate

: 151074-57-6
(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Guidance literature:: With sodium carbonate; at 0 ℃; for 4h;
DOI:10.1016/S0040-4020(01)80152-6

Reference yield:

: 132970-32-2
methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate

: 151074-57-6
(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / diethyl ether / 4 h / Ambient temperature

2: 100 percent / benzophenone / CH₂Cl₂ / 0.3 h / -78 °C

3: 100 percent / 5percent HCl/MeOH / 2.5 h / Ambient temperature

4: 90 percent / tetrahydrofuran / 6 h / Heating

5: 90 percent / 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 20 h / 40 °C

6: 1.) O₃, 2.) Me₂S / 1.) AcOEt, -78 deg C, 20 min, 2.) AcOEt, RT, 30 min

7: 87 percent / NaBH₄ / methanol / 0.33 h / 0 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; sodium tetrahydroborate; benzophenone; dimethylsulfide; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/0957-4166(96)00038-9