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

Base Information

• Chemical Name: (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine
• CAS No.: 127768-10-9
• Molecular Formula: C₂₀H₂₇NO₈S
• Molecular Weight: 441.502
• Mol file: 127768-10-9.mol

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

Chemical Property of (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

There total 8 articles about (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}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: 69.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + (2S,4R)-1-benzyloxycarbonyl-2-(2-oxoethyl)oxymethyl-4-methanesulfonyloxypyrrolidine (127768-11-0) → (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (127768-10-9)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (127768-10-9)

Guidance literature:

Multi-step reaction with 7 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

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; ethyl acetate; toluene;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (117811-78-6) → (2S,4R)-1-benzyloxycarbonyl-2-[{3-[ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (127768-10-9)

Guidance literature:

Multi-step reaction with 6 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

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; toluene;

DOI:10.1016/S0968-0896(97)00142-9

upstream raw materials:

ethyl (triphenylphosphoranylidene)acetate

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

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

Downstream raw materials:

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