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

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

• 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 
• 261962-09-8 (tert-butyldimethylsilanyloxy)-(2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester 
• 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 
• 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 
• 473791-44-5 (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 

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.

Divergent approach to gabosines and anhydrogabosines: Enantioselective syntheses of (+)-epiepoformin, (+)-EpoKformin, (+)-gabosine A, and gabosines B and F

A divergent approach to polyoxygenated methylcyclohexanes has been applied to synthesize several gabosines and anhydrogabosines. The starting hydroxycyclohexenone, which is readily available in any antipodal form, provides access to both enantiomers of the target compounds. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. The strategy has been applied to the synthesis of (+)-epiepoformin, (+)-epoformin, (+)-gabosine A, and gabosines B and F, through straightforward sequences in good overall yields. A cyclohexenone that is easily available in any antipodal form has been used as the starting material to synthesize various gabosines and anhydrogabosines through a divergent strategy. The syntheses of anhydrogabosines involve three main transformations: α-methylation, epoxidation, and sulfur removal, whereas the syntheses of gabosines require an additional epoxide hydrolysis step. Copyright

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