78433-57-5

Basic information

• Product Name: (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether
• Synonyms: (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether
• CAS NO: 78433-57-5
• Molecular Weight: 208.301
• Mol File: 78433-57-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether(78433-57-5)
• EPA Substance Registry System: (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether(78433-57-5)

Safety Data

• Hazardous Substances Data: 78433-57-5(Hazardous Substances Data)

Upstream product

• 16958-19-3 (2E)-2-methyl-2-penten-1-ol 
• 917-54-4 methyllithium 
• 78433-56-4 (2R,3S)-3,4-epoxy-2-methyl-1-butanol benzyl ether 
• 116652-75-6 (R)-1-(benzyloxy)-2-methylpentan-3-one 
• 6061-13-8 (2S,3S)-3-methylaspartic acid 
• 642-92-2 D,L-threo-β-methylaspartic acid 
• 13398-41-9 (2S, 3S)-threo-β-methylmalic acid 
• 86562-33-6 (2S,3R)-threo-3-methylbutane-1,2,4-triol 2-THP ether 
• 78433-53-1 (2S,3S)-dimethyl threo-3-methylmalate THP ether 
• 77333-42-7 (2S,3R)-threo-3-methylbutane-1,2,4-triol 
• 69743-60-8 (2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 
• 50460-80-5 (2S,3S)-2-Hydroxy-3-methyl-bernsteinsaeuredimethylester 
• 78479-15-9 (2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 4-benzyl ether 
• 78479-16-0 (2S,3R)-threo-3-methylbutane-1,2,4-triol 4-benzyl ether 

Downstream Products

• 86562-34-7 (2R,3R)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether 
• 72598-35-7 (-)-serricornin 
• 72485-37-1 (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 
• 82335-98-6 serricornin acetate <(4S,6R,7R)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 83997-86-8 serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 86535-17-3 (2R,3R)-threo-2-methylpentane-1,3-diol 1-tosylate 
• 86562-36-9 (2R,3R)-threo-2-methylpentane-1,3-diol 3-THP ether 1-tosylate 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 100757-47-9 (2S,3S)-3-t-butyldimethylsilyloxy-2-methyl-1-(4-methylbenzenesulfonyloxy)pentane 
• 86535-07-1 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 
• 100699-14-7 (2S,3S)-3-t-butyldimethylsilyloxy-2-methylpentane-1-ol 1-benzyl ether 
• 100699-13-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-3-benzyloxy-1-ethyl-2-methyl-propyl ester 
• 100762-79-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-3-benzyloxy-1-ethyl-2-methyl-propyl ester 
• 72522-40-8 (4RS,6R,7R)-threo-serricornin 

Relevant articles and documents

Versatile enantioselective synthesis of four diastereomers of serricornin, a sex pheromone of the cigarette beetle, using the SAMP/RAMP-hydrazone method

Serricornin is a female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), which is a pest of dried foodstuffs and tobacco. We report a versatile and short synthesis of all possible 6,7-syn-isomers of serricornin, including the natura

A new synthesis of serricornin [(4s,6s,7s)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle

Serricornin, the sex pheromone of Lasioderma serricorne F, was synthesised in 7.6% overall yield starting from methyl (R)-3-hydroxypentanoate of microbial origin. Its (4R,6S,7S)-isomer was also synthesised.

DETERMINATION OF THE ABSOLUTE CONFIGURATION AT C-6 AND C-7 SERRICORNIN (4,6-DIMETHYL-7-HYDROXY-3-NONANONE), THE SEX PHEROMONE OF THE CIGARETTE BEETLE

The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 7S) by synthesizing its (6R, 7S)-erythro and (6R, 7R)-threo isomers.