80971-02-4

Basic information

• Product Name: (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol
• CAS NO: 80971-02-4
• Molecular Weight: 464.558
• Mol File: 80971-02-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol(80971-02-4)
• EPA Substance Registry System: (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol(80971-02-4)

Safety Data

• Hazardous Substances Data: 80971-02-4(Hazardous Substances Data)

Upstream product

• 98925-54-3 (±)-2,3,6-tri-O-benzyl-1,4,5-tri-O-allyl-myo-inositol 
• 111446-91-4 (+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol 
• 98906-29-7 (1R,2S,3R,4R,5S,6R)-2,4,5-Tris-allyloxy-3,6-bis-benzyloxy-cyclohexanol 
• 98906-26-4 (3aR,4R,5S,6S,7R,7aS)-5,6-Bis-allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 98906-34-4 (±)-2,3-O-isopropylidene-1,4-di-O-allyl-6-O-benzyl-myo-inositol 
• 98906-33-3 (±)-1,4-di-O-allyl-2,3-O-isopropylidene-myo-inositol 
• 98906-37-7 (±)-2,3-O-isopropylidene-1,4,5-tri-O-allyl-6-O-benzyl-myo-inositol 
• 111392-09-7 (1S,2R,3S,4R,5R,6S)-3,4,6-Tris-allyloxy-5-benzyloxy-cyclohexane-1,2-diol 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 100-39-0 benzyl bromide 

Downstream Products

• 80971-04-6 1L-1,3,4-Tri-O-benzyl-2-O-methyl-5-O-p-bromphenylsulfonyl-chiro-inosit 
• 484-68-4 1-O-methyl-myo-inositol 
• 22350-68-1 (1R)-1-L-O-methyl-myo-inositol 
• 80971-05-7 1L-1,3,4-Tri-O-benzyl-2-O-methyl-5-O-p-chlorphenylsulfonyl-chiro-inosit 
• 76902-46-0 1L-1,3,4-Tri-O-benzyl-5,6-di-O-methylsulfonyl-2-O-methyl-chiro-inosit 
• 80971-03-5 1L-2,3,4-Tri-O-benzyl-2-O-methyl-5-O-p-tolylsulfonyl-chiro-inosit 

Relevant articles and documents

The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates

Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.

Cyclitol Reactions, V. - Synthesis of Enantiomerically Pure Valienamine from Quebrachitol

An enantioselective synthesis of Valienamine (86) from quebrachitol (L-2O-methyl-chiro-inositol) (1) is described.Valienamine (86) is an unsaturated branched-chain aminocyclitol found in the central structural unit of the antidiabetic drug acarbose.Techniques for the introduction of side chains, azido groups, and double bonds into inositol systems are investigated.The methods developed in this connection are applied in the synthesis of valienamine.