106750-01-0

Basic information

• Product Name: 2,3,4-Trihydroxy-6-methylcyclohexanone
• Synonyms: 2,3,4-Trihydroxy-6-methylcyclohexanone
• CAS NO: 106750-01-0
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• Mol File: 106750-01-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4-Trihydroxy-6-methylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Trihydroxy-6-methylcyclohexanone(106750-01-0)
• EPA Substance Registry System: 2,3,4-Trihydroxy-6-methylcyclohexanone(106750-01-0)

Safety Data

• Hazardous Substances Data: 106750-01-0(Hazardous Substances Data)

Upstream product

• 261962-09-8 (tert-butyldimethylsilanyloxy)-(2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester 
• 473791-40-1 (2R,3R,4aR,7S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-7-methoxymethoxy-2,3,6-trimethyl-octahydro-benzo[1,4]dioxin-5-ol 
• 473791-42-3 (2R,3R,4aS,7S,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-7-methoxymethoxy-2,3,6-trimethyl-hexahydro-benzo[1,4]dioxin-5-one 
• 473791-30-9 (2R,3R,4aS,5R,6S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3-dimethyl-7-methylene-octahydro-benzo[1,4]dioxin-6-ol 
• 473791-44-5 (2R,3R,4aS,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3,6-trimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one 
• 473791-46-7 (2R,3R,4aS,6R,8R,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3,6-trimethyl-hexahydro-benzo[1,4]dioxin-5-one 
• 473791-28-5 ((2R,3R,4aS,5R,8aR)-7-Benzenesulfinylmethyl-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-tert-butyl-dimethyl-silane 
• 473791-32-1 tert-Butyl-((2R,3R,4aS,5R,6S,8aR)-2,3-dimethoxy-6-methoxymethoxy-2,3-dimethyl-7-methylene-octahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane 

Relevant articles and documents

A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization

Gabosines and their natural analogues, belonging to C7 carbasugars, have attracted great attention in synthesis due to their rich structural variety and promising biological activities. A new diversity-oriented approach for the gabosine-type carbasugars based on a tunable regioselective aldol cyclization of flexible precursor 2 is explored. Two cyclization modes (A and B) of the precursor can be well controlled by switching promoters to selectively produce two resulting cyclohexa(e)nones 3 and 10, both of which are versatile intermediates for various C7 carbasugars. After the conversion of 3 to eight natural carbasugars, the utility of intermediate 10 is illustrated by the first synthesis of (-)-gabosine L, as well as the new synthesis of (-)-gabosine A, (-)-gabosine B, (-)-gabosine N and (-)-gabosine O. The chemical structure and the absolute configuration of (-)-gabosine L are confirmed by its total synthesis.

Syntheses of gabosine A, B, D, and E from allyl sulfide derived from (-)-quinic acid

An efficient conversion of allyl sulfide 6 prepared from (-)-quinic acid (5) to gabosines was achieved by a series of sequential reactions: i) Mislow-Evans rearrangement, ii) SeO2 oxidation, iii) conjugate addition of sodium hydroxide or sodium