(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

Base Information

Chemical Name:(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate
CAS No.:1312341-42-6
Molecular Formula:C₁₆H₂₂O₄
Molecular Weight:278.348
Hs Code.:

Synonyms:(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

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Chemical Property of (2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

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Technology Process of (2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

There total 5 articles about (2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate 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: 88.0%

: 1262755-25-8
(S)-4-benzyl-3-((2S,3R)-3-((1S,2S)-2-((benzyloxy)methyl)cyclopropyl)-3-hydroxy-2-methylpropanoyl)-5,5-dimethyloxazolidin-2-one

: 124-41-4
sodium methylate

: 1312341-42-6
(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

Guidance literature:: In methanol; dichloromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;
DOI:10.1021/ol2012023

Reference yield:

: 69152-87-0,122751-47-7,80885-31-0
4-benzyloxybut-2-enal

: 1312341-42-6
(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / dichloromethane / 20 °C

2: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere

3: diethylzinc / hexane; dichloromethane / 2 h / 0 °C / Darkness; Inert atmosphere

4: methanol; dichloromethane / 0.08 h / 20 °C / Inert atmosphere

With di-n-butylboryl trifluoromethanesulfonate; diethylzinc; toluene-4-sulfonic acid; triethylamine; In methanol; hexane; dichloromethane; 2: asymmetric syn-aldol condensation;
DOI:10.1021/ol2012023

Reference yield:

: 81028-03-7
(Z)-4-benzyloxy-but-2-en-1-ol

: 1312341-42-6
(2S,3R)-methyl 3-((1S,2S)-2-(benzyloxymethyl)cyclopropyl)-3-hydroxy-2-methylpropanoate

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 0.5 h / -55 °C

2: toluene-4-sulfonic acid / dichloromethane / 20 °C

3: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere

4: diethylzinc / hexane; dichloromethane / 2 h / 0 °C / Darkness; Inert atmosphere

5: methanol; dichloromethane / 0.08 h / 20 °C / Inert atmosphere

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; diethylzinc; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; hexane; dichloromethane; 3: asymmetric syn-aldol condensation;
DOI:10.1021/ol2012023