115250-39-0

Basic information

• Product Name: Tetrabenzyl-voglibose
• Synonyms: TETRABENZYL-VOGLIBOSE;TBV;1,5,6,7-Tetra-O-benzylvoglibose;Tetrabenzyl-voglibose(TBV);Voglibose TBV Base IMpurity;TBV Tetrabenzyl Voglibose Tetrabenzyl Voglibose;Tetrabenzyl-voglibose(for Voglibose);2-(((1S,2S,3R,4S,5S)-2,3,4-Tris(benzyloxy)-5-((benzyloxy)methyl)-5-hydroxycyclohexyl)amino)propane-1,3-diol
• CAS NO: 115250-39-0
• Molecular Formula: C₃₈H₄₅NO₇
• Molecular Weight: 627.773
• EINECS: 1592732-453-0
• Mol File: 115250-39-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 784.1 °C at 760 mmHg
• Flash Point: 428 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 6.73E-26mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.98±0.70(Predicted)
• CAS DataBase Reference: Tetrabenzyl-voglibose(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabenzyl-voglibose(115250-39-0)
• EPA Substance Registry System: Tetrabenzyl-voglibose(115250-39-0)

Safety Data

• Hazardous Substances Data: 115250-39-0(Hazardous Substances Data)

Usage

Uses

Tetrabenzyl-voglibose is a derivative of Voglibose which is an α-Glucosidase inhibitor used as an antidiabetic.

InChI:InChI=1/C38H45NO7/c40-22-33(23-41)39-34-21-38(42,28-43-24-29-13-5-1-6-14-29)37(46-27-32-19-11-4-12-20-32)36(45-26-31-17-9-3-10-18-31)35(34)44-25-30-15-7-2-8-16-30/h1-20,33-37,39-42H,21-28H2/t34?,35-,36?,37-,38-/m0/s1

Synthetic route

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol (115250-38-9) + serinol (534-03-2) → (1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol (115250-39-0)

Conditions	Yield
With sodium cyanoborohydride In methanol for 16h; Ambient temperature;	75%

tetra-O-benzylvaliolamine (140926-94-9) + serinol (534-03-2) → (1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol (115250-39-0)

Conditions	Yield
Stage #1: tetra-O-benzylvaliolamine; serinol In methanol at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In methanol Stage #3: With hydrogenchloride In methanol; water pH=8.0;

dihydroxyacetone (96-26-4) + tetra-O-benzylvaliolamine (140926-94-9) → (1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol (115250-39-0)

Conditions	Yield
Stage #1: dihydroxyacetone; tetra-O-benzylvaliolamine In methanol at 20 - 30℃; for 0.5 - 1h; Stage #2: With hydrogenchloride; sodium cyanoborohydride In methanol; water pH=~ 6.0; Product distribution / selectivity;

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol (115250-39-0) → voglibose (83480-29-9)

Conditions	Yield
With formic acid; palladium In methanol Ambient temperature;	94%
With boron trifluoride diethyl etherate; diisopropylamine In tetrahydrofuran at 15 - 30℃; Reagent/catalyst; Solvent;	82.86%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In tetrahydrofuran; methanol; water at 20℃; under 2206.72 - 2574.5 Torr; for 3h;

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol (115250-39-0) → 4-benzyl-voglibose + voglibose (83480-29-9)

Conditions	Yield
With formic acid; palladium on activated charcoal In methanol; water Inert atmosphere;	A 0.7 g B 16 g

Upstream product

• 116308-18-0 (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol 
• 140658-50-0 (2R,3R,4S,5R,6R)-3,4,5-tris-benzyl-6-benzyloxymethyl-2-dichloromethyltetrahydro-2H-pyran-2-ol 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 96-26-4 dihydroxyacetone 
• 140926-94-9 tetra-O-benzylvaliolamine 
• 534-03-2 serinol 
• 115250-38-9 (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol 

Downstream Products

• 83480-29-9 voglibose 

Relevant articles and documents

Synthesis method of voglibose

The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.

Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives

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