(2S,4R)-4-Tosyloxy-2-tosyloxymethyl-1-pyrrolidinecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4R)-4-Tosyloxy-2-tosyloxymethyl-1-pyrrolidinecarboxylic acid tert-butyl ester
• CAS No.: 61478-27-1
• Molecular Formula: C24H31NO8S2
• Molecular Weight: 525.644
• DSSTox Substance ID: DTXSID601103453
• Nikkaji Number: J25.946B
• Mol file: 61478-27-1.mol

Synonyms:61478-27-1;tert-Butyl (2S,4R)-4-(tosyloxy)-2-((tosyloxy)methyl)pyrrolidine-1-carboxylate;(2S,4R)-4-(Toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester;SCHEMBL1366652;MCIYOWPKJANFDO-VQTJNVASSA-N;DTXSID601103453;CS-0103542;(2S,4R)-4-Tosyloxy-2-tosyloxymethyl-1-pyrrolidinecarboxylic acid tert-butyl ester;(2S,4R)-tert-butyl 4-(tosyloxy)-2-(tosyloxymethyl)pyrrolidine-1-carboxylate;1,1-Dimethylethyl (2S,4R)-4-[[(4-methylphenyl)sulfonyl]oxy]-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylate

Chemical Property of (2S,4R)-4-Tosyloxy-2-tosyloxymethyl-1-pyrrolidinecarboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 654.4±50.0 °C(Predicted)
• PSA: 133.04000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 5.89170
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 525.14910929
• Heavy Atom Count: 35
• Complexity: 916

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CC(CN2C(=O)OC(C)(C)C)OS(=O)(=O)C3=CC=C(C=C3)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]2C[C@H](CN2C(=O)OC(C)(C)C)OS(=O)(=O)C3=CC=C(C=C3)C

Technology Process of (2S,4R)-4-Tosyloxy-2-tosyloxymethyl-1-pyrrolidinecarboxylic acid tert-butyl ester

There total 10 articles about (2S,4R)-4-Tosyloxy-2-tosyloxymethyl-1-pyrrolidinecarboxylic acid tert-butyl 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: 83.0%

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0) + p-toluenesulfonyl chloride (98-59-9) → (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine (61478-27-1)

Guidance literature:

In pyridine; at 0 - 5 ℃; for 24h;

DOI:10.1021/jo01311a036

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine (61478-27-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / HCl / 2 h / Heating

2: 69.6 percent / Et₃N / dioxane; H₂O / 15 h / 50 °C

3: 81 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h

4: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days

With hydrogenchloride; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; water;

DOI:10.1021/jo00327a023

Reference yield:

(2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (37813-30-2) → (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine (61478-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h

2: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days

With lithium aluminium tetrahydride; In tetrahydrofuran; pyridine;

DOI:10.1021/jo00327a023

upstream raw materials:

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

p-toluenesulfonyl chloride

N-(tert-butyloxycarbonyl) azide

trans-4-hydroxy-L-proline ethyl ester hydrochloride

Downstream raw materials:

(2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine

(1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane

(2S,4S)-N-tert.-butoxycarbonyl-4-bis(2-methoxyphenyl)phosphino-2-bis(2-methoxyphenyl)phosphinomethylpyrrolidine

2-benzyl-2,5-diazabicyclo[2.2.1]heptane dihydrochloride

Refernces

• 1、 -. "HDAC INHIBITORS AND USES THEREOF". Page/Page column 48-49. . Retrieved 2010/01/29.
• 2、 Baker, Gregory L.,Fritschel, Scott J.,Stille, John R.,Stille, John K.. "Transition-Metal-Catalyzed Asymmetric Organic Synthesis via Polymer-Attached Optically Active Phosphine Ligands. 5. Preparation of Amino Acids in High Optical Yield via Catalytic Hydrogenation". . p. 2954 - 2960. Retrieved 2007/10/02.