126661-83-4

Basic information

• Product Name: cyclophellitol
• Synonyms: cyclophellitol;(1R,2S)-1β,2β-Epoxy-6β-hydroxymethylcyclohexane-3α,4β,5α-triol;(1S,2R,3S,4R,5R,6R)-5-(Hydroxymethyl)-7-oxabicyclo[4.1.0]heptane-2,3,4-triol;5-Hydroxymethyl-7-oxabicyclo(4,1,0)heptane-2,3,4-triol;D-Myo-inositol, 1,2-anhydro-3-deoxy-3-(hydroxymethyl)-;Epi-cpl
• CAS NO: 126661-83-4
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.16718
• Mol File: 126661-83-4.mol

Chemical Properties

• Boiling Point: 392.4°Cat760mmHg
• Flash Point: 191.1°C
• Appearance: /
• Density: 1.665g/cm³
• Vapor Pressure: 8.83E-08mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: cyclophellitol(CAS DataBase Reference)
• NIST Chemistry Reference: cyclophellitol(126661-83-4)
• EPA Substance Registry System: cyclophellitol(126661-83-4)

Safety Data

• Hazardous Substances Data: 126661-83-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H12O5/c8-1-2-3(9)4(10)5(11)7-6(2)12-7/h2-11H,1H2/t2-,3-,4+,5-,6-,7+/m1/s1

Upstream product

• 139402-99-6 (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate 
• 128184-64-5 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside 
• 128184-62-3 (2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran 
• 138875-24-8 methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside 
• 138794-98-6 Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester 
• 128184-67-8 (2S,3R,4S,5R,6R)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone 
• 128184-66-7 (1R,2R,3S,4S,5R)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene 
• 128184-63-4 methyl 2,3,4-tri-O-benzyl-β-D-idopyranoside 
• 161596-05-0 (1S,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol 
• 161596-04-9 (1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol 
• 151693-61-7 (1S,2R,3R,4R)-1-O-benzoyl-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol 
• 151693-59-3 (1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4-tetraol 
• 151693-57-1 (1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidenecyclohexane-1,2,3,4-tetraol 
• 151693-60-6 (1R,2R,3R,4S,6R)-1,2-di-O-benzyl-6-benzyloxymethyl-4-phenylselenocyclohexane-1,2,3-triol 

Downstream Products

• 136861-99-9 (1S,2R,3S,4R,5R,6R)-2,3,4-tris(benzyloxy)-5-benzyloxymethyl-7-oxabicyclo<4.1.0>heptane 
• 77154-90-6 DL-hexa-O-acetyl-(1,3,4/2,5,6)-6-hydroxymethyl-1,2,3,4,5-cyclohexanepentol 
• 77144-69-5 DL-Penta-O-acetyl-(1,3,4/2,5,6)-5-azido-6-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol 
• 77144-70-8 DL-Penta-O-acetyl-(1,3,4/2,5,6)-5-azetamido-6-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol 
• 154335-63-4 (1R,2R,3S,4R,5R,6S)-2,3,4-Tris-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-7-thia-bicyclo[4.1.0]heptane 
• 154335-62-3 (1S,2S,3S,4R,5R,6S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-7-aza-bicyclo[4.1.0]heptane 

Relevant articles and documents

Total syntheses of (±)-cyclophellitol and (1R°,6S°)-cyclophellitol

A stereodivergent synthesis of (+)-cyclophellitol (1) and its unnatural diastereoisomer (1R*6S*)-cyclophellitol (2), starting from the Diels-Alder adduct of furan and acrylic acid, is reported. The stereochemistry of the key step, the epoxidation of alkene 7, is controlled by the nature of the hydroxyl protecting groups.

Synthesis and evaluation of hydroxymethylaminocyclitols as glycosidase inhibitors

Four series of C7N aminocyclitol analogues of glucose were synthesized by stereocontrolled epoxide opening of hydroxyl protected forms of the cyclohexane epoxides cyclophellitol and 1,6-epi-cyclophellitol. The resulting hydroxymethyl substitute

Synthesis of cyclophellitol, cyclophellitol aziridine, and their tagged derivatives

Cyclitol epoxides and aziridines are potent and selective irreversible inhibitors of retaining glycosidases. We have previously reported on our studies on the use of activity-based probes derived from cyclophellitol and from its aziridine analogue for activity-based profiling of retaining β-glucosidases in vitro, in situ, and in some examples also in vivo. In this work we disclose full details of the synthesis, purification, and analysis of a comprehensive panel of cyclophellitol analogues, all featuring the β-glucose configuration and designed as tools for selective inhibition and/or imaging of human acid glucosylceramidase (epoxides) or as broad-spectrum probes for retaining β-glucosidases (aziridines).

Vinylogy in orthoester hydrolysis: Total syntheses of cyclophellitol, valienamine, gabosine K, valienone, gabosine G, 1-epi-streptol, streptol, and uvamalol A

C7-cyclitols represent an important category of natural products possessing a broad spectrum of biological activities. As each member of these compounds is structurally unique, the usual practice is to synthesize them individually from appropriate polyhydroxylated chiral pools. We have observed an unusual vinylogy in acid mediated hydrolysis of enol ethers of myo-inositol 1,3,5-orthoesters giving a synthetically versatile polyhydroxylated cyclohexenal intermediate. We have exploited this unprecedented reaction for developing a general strategy for the rapid and efficient syntheses of several structurally diverse natural products of C7-cyclitol family. We have made an appropriately protected advanced intermediate 25 in five steps from the cheap and commercially available myo-inositol, and this common intermediate has been used to synthesize eight natural products in racemic form. We could synthesize (±)-cyclophellitol in seven steps, (±)-valienamine in five steps, (±)-gabosine I in five steps, (±)-gabosine G in six steps, (±)-gabosine K in three steps, (±)-streptol in six steps, (±)-1-epi-streptol in two steps, and (±)-uvamalol A in five steps from this intermediate.

A novel chemo-multienzymatic synthesis of bioactive cyclophellitol and epi-cyclophellitol in both enantiopure forms

A new route to synthesize cyclophellitol and epi-cyclophellitol from racemic starting materials in enantiopure forms has been developed. The synthesis involves a multi-enzymatic biotransformation pathway of the novel cyano-cyclitol (1R,4S,5R,6R)/(1S,4R,5S

Synthesis of cyclophellitol utilizing a palladium chloride mediated-ferrier-II rearrangement

Cyclophellitol and its C3-epimer have been synthesized from 5-enoglucopyranoside and 5-enomannopyranoside, respectively. The carbocyclic skeleton was constructed through a Ferrier-II reaction meditated by PdCl 2.

A short synthesis of (+)-cyclophellitol

A new synthesis of (+)-cyclophellitol, a potent β-glucosidase inhibitor, has been completed in nine steps from D-xylose. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 5-deoxy-5-iodo-xylofuranoside followed by a h

Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

(Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cyclo

AAA in KAT/DYKAT processes: First- and second-generation asymmetric syntheses of (+)- and (-)-cyclophellitol

Kinetic resolutions and kinetic asymmetric transformations (KAT) as well as dynamic kinetic resolutions and dynamic kinetic asymmetric transformations (DYKAT) are important synthetic protocols. The feasibility of KAT and DYKAT processes for asymmetric all

Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol

Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue.