111080-13-8

Basic information

• Product Name: 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane
• Synonyms: 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane
• CAS NO: 111080-13-8
• Molecular Weight: 675.222
• Mol File: 111080-13-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane(111080-13-8)
• EPA Substance Registry System: 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane(111080-13-8)

Safety Data

• Hazardous Substances Data: 111080-13-8(Hazardous Substances Data)

Upstream product

• 115393-78-7 (2R,5S)-5-<(R)-2,4-bis(benzyloxy)-1,1-dimethylbutyl>-2-methyl-5-pentanolide 
• 115378-60-4 (2S,3R,6S)-6-<(R)-2,4-bis(benzyloxy)-1,1-dimethylbutyl>tetrahydro-2-methoxy-3-methyl-2H-pyran 
• 115378-52-4 (4S,6R)-6,8-bis(benzyloxy)-5,5-dimethyl-1-octen-4-ol 
• 115378-57-9 Propionic acid (1S,3R)-3,5-bis-benzyloxy-2,2-dimethyl-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyl ester 
• 115378-58-0 (1S,3R)-3,5-bis(benzyloxy)-1-(2-iodoethyl)-2,2-dimethylpentyl propionate 
• 115378-56-8 Propionic acid (1S,3R)-3,5-bis-benzyloxy-1-(2-hydroxy-ethyl)-2,2-dimethyl-pentyl ester 
• 115378-55-7 Propionic acid (1S,3R)-3,5-bis-benzyloxy-2,2-dimethyl-1-(2-oxo-ethyl)-pentyl ester 
• 115378-54-6 Propionic acid (1S,3R)-1-allyl-3,5-bis-benzyloxy-2,2-dimethyl-pentyl ester 
• 115378-63-7 Toluene-4-sulfonic acid (R)-3-hydroxy-4-((2S,5R,6S)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-4-methyl-pentyl ester 
• 115378-62-6 (R)-4-((2S,5R,6S)-6-Methoxy-5-methyl-tetrahydro-pyran-2-yl)-4-methyl-pentane-1,3-diol 
• 109-80-8 1.3-propanedithiol 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 115378-66-0 (2S,3R,6S)-6-<(R)-2-(tert-butyldimethylsilyloxy)-1,1-dimethyl-4-(phenylsulfonyl)butyl>tetrahydro-2-methoxy-3-methyl-2H-pyran 
• 115378-59-1 (S)-6-((R)-2,4-Bis-benzyloxy-1,1-dimethyl-butyl)-3-methyl-tetrahydro-pyran-2-one 

Downstream Products

• 115378-67-1 (4R,6S,9R)-2-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-9-[1,3]dithian-2-yl-5,5-dimethyl-1-((2S,4S,5R)-5-methyl-4-triisopropylsilanyloxy-tetrahydro-furan-2-yl)-decan-1-ol 
• 111080-20-7 Benzoic acid (4R,6S,9R)-2-benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-9-[1,3]dithian-2-yl-5,5-dimethyl-1-((2S,4S,5R)-5-methyl-4-triisopropylsilanyloxy-tetrahydro-furan-2-yl)-decyl ester 

Relevant articles and documents

A FORMAL SYNTHESIS OF APLASMOMYCIN. ASSEMBLY OF THE C3-C17 SEGMENT BASED ON 1,3- AND 1,5- ASYMMETRIC REDUCTIONS

The C3 - C17 segment of a boron containing ionophoric antibiotic aplasmomycin (1), the key intermediate in Corey's total synthesis of 1, was stereoselectively synthesized in an optically active form.This synthesis involved stereoselective construction of the two segments, (+)-dithiane 3 (C3-C11) and (+)-aldehyde 4 (C12-C17), based on remote controlled asymmetric reductions of the corresponding ketones as key steps and connection of 3 and 4 through the trans-double bond to elaborate the (+)-dithiane 2 (C3-C17), the key intermediate in Corey's total synthesis of 1.

SYNTHETIC STUDIES ON (+)-APLASMOMYCIN. 2. STEREOSELECTIVE SYNTHESIS OF COREY'S KEY INTERMEDIATE, A FORMAL TOTAL SYNTHESIS

The C-3 - C-11 segment 2 of (+)-aplasmomycin was synthesized stereoselectively starting from (+)-pantolactone (4) and the C-3 - C-17 segment 3 was synthesized via coupling of 1 and 2.