90695-22-0

Basic information

• Product Name: (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate
• Synonyms: (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate
• CAS NO: 90695-22-0
• Molecular Weight: 388.372
• Mol File: 90695-22-0.mol

Chemical Properties

• CAS DataBase Reference: (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate(90695-22-0)
• EPA Substance Registry System: (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate(90695-22-0)

Safety Data

• Hazardous Substances Data: 90695-22-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 90695-20-8 (1S)-2-exo,3-endo-diacetoxy-5-endo-acetoxymethyl-7-oxabicyclo<2.2.1.>heptane 
• 104976-78-5 1L-(1,3,5/2,4)-2,3,4-Tri-O-benzyl-5-C-hydroxymethyl-1,2,3,4-cyclohexantetrol 
• 219623-01-5 2,3,4,6-tetra-O-acetyl-1-deoxy-1-methylene-5a-carba-D-glucopyranose 
• 282101-78-4 (1R,4R,5S,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-2-enol 
• 102562-04-9 (1R,3R,4S,5S,6S,8R,9R)-3,4,5-trihydroxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane 
• 102562-02-7 (1R,3R,4R,5S,6S,8R,9R)-4,5-epoxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonan-3-ol 
• 102562-01-6 (1R,4S,5S,6S,8R,9R)-4,5-epoxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonan-3-one 
• 112473-48-0 (3S,4S,5R)-3,4,5-Tris-benzyloxy-cyclohex-1-enecarbaldehyde 
• 112473-47-9 (1R,2S,3S,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxycyclohexanecarbaldehyde 
• 112531-56-3 (3S,4S,5R)-3,4,5-tris(benzyloxy)-1-cyclohexene-1-methanol 
• 90760-56-8 (-)-7-endo-oxabicyclo<2.2.1>hept-5-ene-2-carboxylic acid 
• 24363-23-3 (+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 
• 97747-50-7 (3R)-(+)-2-exo-hydroxy-4,8-dioxatricyclo<4.2.1.0^3,7>nonan-5-one 

Downstream Products

• 86117-82-0 (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol 
• 10226-73-0 Pseudo-α-DL-talopyranose; 2c,3c,4c,5t-Tetrahydroxy-1-cyclohexan-methanol 
• 97321-82-9 (1SR,3SR,5SR,8RS,10SR,12RS)-5,12-diphenyl-4,6,11,13-tetraoxatricyclo<8.3.0.0^3,8>tridecan-2-one 
• 97321-80-7 (1SR,2RS,3SR,5SR,8RS,10SR,12RS)-5,12-diphenyl-4,6,11,13-tetraoxatricyclo<8.3.0.0^3,8>tridecan-2-ol 
• 97321-80-7 (1SR,2SR,3SR,5SR,8RS,10SR,12RS)-5,12-diphenyl-4,6,11,13-tetraoxatricyclo<8.3.0.0^3,8>tridecan-2-ol 
• 97321-80-7 (1SR,2SR,3SR,5SR,8RS,10SR,12SR)-5,12-diphenyl-4,6,11,13-tetraoxatricyclo<8.3.0.0^3,8>tridecan-2-ol 
• 10226-73-0 DL-(1,5/2,3,4)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 
• 10226-79-6 DL-(1,5/2,3,4)-5-acetoxymethyl-1,2,3,4-tetra-acetoxycyclohexane 
• 10226-73-0 (1S,2S,3S,4S,5S)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol 
• 10226-73-0 (1R,2S,3S,4R,5S)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol 
• 10226-73-0 DL-(1,2,3/4,5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 
• 10226-73-0 DL-(1,2,3,4/5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 
• 80065-33-4 DL-tetra-O-acetyl-(1,3,5/2,4)-5-acetamidomethyl-1,2,3,4-cyclohexanetetrol 
• 60543-79-5 DL-tetra-O-acetyl-(1,3,5/2,4)-5-methyl-1,2,3,4-cyclohexanetetrol 

Relevant articles and documents

Synthetic strategies directed towards 5a-carbahexopyranoses and derivatives based on 6-endo-trig radical cyclizations

Several synthetic strategies directed towards 5a-carbahexopyranoses and based on 6-endo-trig radical cyclization of unsaturated carbohydrate derivatives have been devised. Three elements for regiocontrol to optimize the 6-endo/5-exo ratio have been incorporated, and their efficiencies in directing 6-endo cyclizations have been evaluated. These elements - namely: i) the incorporation of a substituent at C-5 (radical numbering), ii) the use of a vinyl (rather than alkyl) radical, and iii) the inclusion of ring strain in the system - have proved useful when used in combination. The simultaneous presence of two of them also results in 6-endo selectivity. On another topic, the ozonation of the ensuing alkenylstananes to afford diols seems to be based on a tin-oxygen rearrangement, similar to that reported for related vinylsilanes, rather than on remarkable stabilities of tin-containing primary ozonides as we had previously suggested.

Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside

For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.

A general norbornyl based synthetic approach to carbasugars and 'confused' carbasugars

The norbornyl system has been recognized simply as a 'locked' carbasugar and a short, general approach to carbasugars and their new siblings, 'confused' carbasugars, from readily available 7-ketonorbornanes is reported.

A norbornyl route to cyclohexitols: Structural diversity in fragmentation through functional group switching. Synthesis of α- and β- galactose, α-talose and α-fucopyranose carbasugars

A novel fragmentation sequence has been executed within the norbornane system, involving C1-C7 bond scission, to extract a versatile, highly functionalized cyclohexanoid moiety. Its further evolution towards a range-of carbasugars is described. (C) 2000 Elsevier Science Ltd.

A Novel Transformation of Four Aldoses to Some Optically Pure Pseudohexopyranoses and a Pseudopentofuranose, Carboxylic Analogues of Hexopyranoses and Pentofuranose. Synthesis of Derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,

Knoevenagel reactions with dimethyl malonate of the suitably protected acylic aldehydes 6, 20, 34, and 46, which were prepared from D-ribose, D-xylose, D-arabinose, and D-erythrose, respectively, proceeded smoothly to provide α,β-unsaturated diesters 7, 2

Construction of an Optically Active 7-Oxabicyclonon-4-en-3-one. Skeleton from D-Glucose, and Its Transformation to Some Pseudo-Hexopyranoses

A versatile chiral compound, (1R,6R,8R,9R)-8,9-isopropylidenedioxy-7-oxabicyclonon-4-en-3-one (6), was efficiently synthesized from D-glucose.The synthesis featured an intramolecular aldol cyclization of 3-C-acetylmethyl-3-deoxy-1,2-O-isopropyliden