153381-09-0

Basic information

• Product Name: 3,5-Heptanediol, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (3R,5S)-
• CAS NO: 153381-09-0
• Molecular Formula: C21H28O6
• Molecular Weight: 376.45
• Mol File: 153381-09-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3,5-Heptanediol, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (3R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Heptanediol, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (3R,5S)-(153381-09-0)
• EPA Substance Registry System: 3,5-Heptanediol, 1,7-bis(4-hydroxy-3-methoxyphenyl)-, (3R,5S)-(153381-09-0)

Safety Data

• Hazardous Substances Data: 153381-09-0(Hazardous Substances Data)

Upstream product

• 1360109-97-2 (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxypentan-1-one 
• 1360109-98-3 (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-(methoxymethoxy)pentan-1-one 
• 1360110-00-4 (S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-(methoxymethoxy)pentanal 
• 1360110-02-6 (S)-1,7-bis(4-(benzyloxy)-3-methoxyphenyl)-5-(methoxymethoxy)hept-1-yn-3-one 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 57371-44-5 3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol 
• 38157-08-3 (E)-3-(4-benzyloxy-3-methoxyphenyl)acrylic acid ethyl ester 
• 36062-05-2 (S)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one 
• 69172-20-9 3-(3-methoxy-4-benzyloxyphenyl)propionaldehyde 
• 144735-54-6 1-ethynyl-4-(benzyloxy)-3-methoxybenzene 
• 1360110-05-9 (S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(methoxymethoxy)heptan-3-one 
• 458-37-7 curcumin 
• 135308-87-1 meso-3,5-Diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 

Relevant articles and documents

Synthesis of gingerol and diarylheptanoids

The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds.

Stereo-conserved synthesis of syn-diarylheptanoids, active principles of Zingiber, starting from d-glucose

A highly efficient and stereo-controlled synthetic strategy has been developed to access syn-diarylheptanoids, for example, 2, 3, 4, and 5b starting from d-glucose as a chiral pool. The 3-(R), 5-(S)-syn-diol stereochemistry present in these heptanoids was obtained after conserving C2 and C4 stereochemistry of d-glucose during the course of synthetic transformation. The key features of this synthetic strategy include: (i) conversion of d-glucose to a known chiral template 6 armored with the required 1,3-syn-diol stereochemistry as well as two terminal aldehyde functionalities for building up customized 'diaryl wings'; (ii) conversion of 6 to 7 via an initial Wittig olefination at the C5-aldehyde; (iii) use of the hemiacetal 7 as a common intermediate to obtain the individual heptanoids via a second Wittig reaction at its anomeric center using appropriately chosen ylides.