(2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine

Base Information

• Chemical Name: (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine
• CAS No.: 117811-79-7
• Molecular Formula: C₁₄H₁₉NO₆S
• Molecular Weight: 329.374
• DSSTox Substance ID: DTXSID601124922
• Mol file: 117811-79-7.mol

Synonyms:117811-79-7;SCHEMBL9372895;QQGZOHNKVFKZOS-QWHCGFSZSA-N;DTXSID601124922;(2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine;Benzyl (2S,4R)-2-(hydroxymethyl)-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate;Phenylmethyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate

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

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 329.09330850
• Heavy Atom Count: 22
• Complexity: 468

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CS(=O)(=O)OC1CC(N(C1)C(=O)OCC2=CC=CC=C2)CO
• Isomeric SMILES: CS(=O)(=O)O[C@@H]1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)CO

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

There total 5 articles about (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-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: 100.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (117811-78-6) → (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (117811-79-7)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 6h;

Reference yield:

(2S,4R)-4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (117811-87-7) → (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (117811-79-7)

Guidance literature:

With sodium borohydrid; trifluoroborane diethyl ether; In tetrahydrofuran; acetic acid;

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (117811-79-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; ethanol; ethyl acetate;

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

upstream raw materials:

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

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

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

(2S,4R)-4-(methanesulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Downstream raw materials:

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

(2S,4R)-1-benzyloxycarbonyl-2-(carboxymethyloxymethyl)-4-methanesulfonyloxypyrrolidine

(2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine

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