(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Base Information

Chemical Name:(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine
CAS No.:127768-11-0
Molecular Formula:C₁₆H₂₁NO₇S
Molecular Weight:371.411
Hs Code.:

Synonyms:(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

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Chemical Property of (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Chemical Property:

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Technology Process of (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

There total 8 articles about (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine 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:

: 79-37-8
oxalyl dichloride

: 127768-04-1
(2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine

: 127768-11-0
(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Guidance literature:: With dimethyl sulfoxide; triethylamine; In dichloromethane; water; ethyl acetate;

Reference yield:

: 64187-48-0
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

: 127768-11-0
(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / ethyl acetate / 0.5 h / 0 - 5 °C

2: NaBH₄ / tetrahydrofuran; ethanol / 2 h / 25 - 30 °C

3: t-BuOK / tetrahydrofuran / 1 h / -10 - -5 °C

4: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

5: 86 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / 1.5 h / -10 - 10 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 15 min, 2.) CH₂Cl₂, -70 deg C, 2 h

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; ethyl acetate;
DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

: 117811-78-6
methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

: 127768-11-0
(2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / tetrahydrofuran; ethanol / 2 h / 25 - 30 °C

2: t-BuOK / tetrahydrofuran / 1 h / -10 - -5 °C

3: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

4: 86 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / 1.5 h / -10 - 10 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 15 min, 2.) CH₂Cl₂, -70 deg C, 2 h

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol;
DOI:10.1016/S0968-0896(97)00142-9