(2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester
• CAS No.: 213763-12-3
• Molecular Formula: C₂₉H₄₃NO₈SSi
• Molecular Weight: 593.814
• Mol file: 213763-12-3.mol

Synonyms:(2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

Chemical Property of (2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

There total 1 articles about (2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl 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:

(toluene-4-sulfonylamino)acetic acid benzyl ester (63366-76-7) + (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (108817-97-6) → (2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester (213763-12-3) + (2R,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

Guidance literature:

With tin(ll) chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1833::aid-ejoc1833>3.0.co;2-f

Reference yield: 70.0%

3,4-dihydro-2H-pyran (110-87-2) + (2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester (213763-12-3) → (S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1833::aid-ejoc1833>3.0.co;2-f

Reference yield:

(2S,3S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester (213763-12-3) → (S)-3-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid benzyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2: 63 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1833::aid-ejoc1833>3.0.co;2-f

upstream raw materials:

(toluene-4-sulfonylamino)acetic acid benzyl ester

(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde