(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside

Base Information

• Chemical Name: (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside
• CAS No.: 1289154-21-7
• Molecular Formula: C₄₁H₄₉NO₇S
• Molecular Weight: 699.909
• Mol file: 1289154-21-7.mol

Synonyms:(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside

Chemical Property of (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside

There total 12 articles about (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside 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%

(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propan-1-ol (1289154-19-3) + O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (120703-59-5) → (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside (1289154-21-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -30 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1515/HC.2010.16.2-3.105

Reference yield:

(-)methyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propionate (1289154-18-2) → (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside (1289154-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 - 20 °C

1.2: 1 h

2.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / -30 °C / Inert atmosphere; Molecular sieve

With lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; In diethyl ether;

DOI:10.1515/HC.2010.16.2-3.105

Reference yield:

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → (-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propyl-2,3,4-tri-O-benzyl-β-L-fucopyranoside (1289154-21-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Dowex-H⁺ / 24 h / 75 °C

2: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 20 °C

3: methanol; palladium dichloride / 2 h / 20 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

5: trimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / -30 °C / Inert atmosphere; Molecular sieve

With methanol; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1515/HC.2010.16.2-3.105

upstream raw materials:

(-)dimethyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]methyl malonate

(-)methyl [(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propionate

(-)-[(S)-N-(p-tolylsulfonyl)-2-pyrrolidinyl]propan-1-ol

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate