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

Base Information

Chemical Name:(2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine
CAS No.:127768-12-1
Molecular Formula:C₁₈H₂₅NO₇S
Molecular Weight:399.465
Hs Code.:

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

Suppliers and Price of (2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 9 articles about (2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)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: 56.0%

: 127768-10-9
(2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

: 127768-12-1
(2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

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

: 127768-12-1
(2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Guidance literature:: Multi-step reaction with 8 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

7: 69 percent / toluene / 3 h / Heating

8: 56 percent / DIBAH / tetrahydrofuran / 0 °C

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

Reference yield:

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

: 127768-12-1
(2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Guidance literature:: Multi-step reaction with 7 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

6: 69 percent / toluene / 3 h / Heating

7: 56 percent / DIBAH / tetrahydrofuran / 0 °C

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