(2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

Base Information

Chemical Name:(2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester
CAS No.:155433-61-7
Molecular Formula:C₁₅H₂₀O₅
Molecular Weight:280.321
Hs Code.:

Synonyms:(2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

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Chemical Property of (2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

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Technology Process of (2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

There total 5 articles about (2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric 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: 90.0%

: 67-56-1
methanol

: 137532-03-7
(2S,3S,4S,5R)-6-benzyloxy-2-hydroxy-5-iodo-3-methylhexan-4-olide

: 155433-61-7
(2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

Guidance literature:: With sodium carbonate; for 48h; Ambient temperature;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 14869-02-4,110339-29-2,120575-96-4,132154-81-5,132340-20-6,143729-23-1,110339-30-5
R-(E)-1-(benzyloxy)pent-3-en-2-ol

: 155433-61-7
(2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydride / tetrahydrofuran / 12 h / Heating

2: Na₂CO₃ / H₂O; hexamethylphosphoric acid triamide / 12 h

3: 1.) LDA; 2.) Cp₂TiCl₂ / 1.) THF, hexane, -100 deg C, 1 h; 2.) THF, -100 deg C, 15 min then -20 deg C, 19 h

4: aq. KOH; methanol / 24 h / Ambient temperature

5: iodine / acetonitrile / 18 h / 0 °C

6: 90 percent / Na₂CO₃ / 48 h / Ambient temperature

With bis(cyclopentadienyl)titanium dichloride; iodine; sodium hydride; sodium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; water; acetonitrile;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 120575-88-4
isopropyl <(1R,2E)-1-benzyloxymethyl-2-butenyloxy>acetate

: 155433-61-7
(2S,3S)-3-((2S,3S)-3-Benzyloxymethyl-oxiranyl)-2-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA; 2.) Cp₂TiCl₂ / 1.) THF, hexane, -100 deg C, 1 h; 2.) THF, -100 deg C, 15 min then -20 deg C, 19 h

2: aq. KOH; methanol / 24 h / Ambient temperature

3: iodine / acetonitrile / 18 h / 0 °C

4: 90 percent / Na₂CO₃ / 48 h / Ambient temperature

With bis(cyclopentadienyl)titanium dichloride; iodine; sodium carbonate; lithium diisopropyl amide; In methanol; potassium hydroxide; acetonitrile;
DOI:10.1016/S0040-4020(01)81547-7