157982-25-7

Basic information

• Product Name: (1R)-tetrahydropyran-(2RS)-2-yl [(1R,3R)-1-(1,3-dithiane-1,3-dioxide-2-yl)-1-phenyl]methyl ether
• Synonyms: (1R)-tetrahydropyran-(2RS)-2-yl [(1R,3R)-1-(1,3-dithiane-1,3-dioxide-2-yl)-1-phenyl]methyl ether
• CAS NO: 157982-25-7
• Molecular Weight: 342.48
• Mol File: 157982-25-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R)-tetrahydropyran-(2RS)-2-yl [(1R,3R)-1-(1,3-dithiane-1,3-dioxide-2-yl)-1-phenyl]methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-tetrahydropyran-(2RS)-2-yl [(1R,3R)-1-(1,3-dithiane-1,3-dioxide-2-yl)-1-phenyl]methyl ether(157982-25-7)
• EPA Substance Registry System: (1R)-tetrahydropyran-(2RS)-2-yl [(1R,3R)-1-(1,3-dithiane-1,3-dioxide-2-yl)-1-phenyl]methyl ether(157982-25-7)

Safety Data

• Hazardous Substances Data: 157982-25-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 110-87-2 3,4-dihydro-2H-pyran 
• 158060-53-8 (1R,3R)-1,3-dithiane-1,3-dioxide-2-[(1R)-1-phenyl]methanol 

Downstream Products

• 199870-96-7 (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate 
• 157982-31-5 (R)-S-ethyl hydroxy-phenyl-thioacetate 
• 79546-40-0 (S)-2-(2-Hydroxy-2-phenyl-acetylamino)-propionic acid methyl ester 
• 20698-91-3 (R)-methyl mandelate 
• 611-71-2 (R)-Mandelic Acid 
• 157982-28-0 (1R)-S-ethyl [1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]-thioacetate 
• 199989-09-8 S-[[(1R)-1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]thioacetyl]-S-propyl[[(1R)-1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]thioacetyl]-S-propanethiosulfinate 
• 133867-57-9 (R)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester 

Relevant articles and documents

trans-1,3-dithiane-1,3-dioxide; a chiral acyl anion equivalent. Enantioselective synthesis of α-hydroxy- carboxylic acids, esters, amides and ketones

The reaction of (R,R)-(+)-1,3-dithiane-1,3-dioxide with aldehydes has been carried out and the dithiane dioxide moiety elaborated further. (R,R)-(+)-1,3-Dithiane-1,3-dioxide gave highly diastereoselective addition products with benzaldehyde and 3,4- dimethoxybenzaldehyde and single diastereomers were isolated in 84 and 76% purified yields respectively. Under similar conditions cyclohexane carboxaldehyde gave an easily separable mixture of diastereomers in 86% total isolated yield. The adducts were transformed into protected S- ethyl α-hydroxythioesters in 95-100% ee via a Pummerer reaction and subsequent trans-thioesterification protocol using LiSEt. Using LiSEt little racemisation occurred even with aryl substituted thioesters. Further transformations of thioesters to various α-hydroxy carboxylic acid derivatives (acids, esters, amides) without racemisation have been achieved. The approach resulted in the synthesis of the dimethyl ether of (R)-(-)-3,4-dihydroxymandelic acid in its naturally occurring form. Addition of dibutyl cuprate (derived from BuMgBr and Cu(I)Br) to the thioester gave the corresponding ketone in high yield and again without racemisation.