2-({(2S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexyl}amino)propane-1,3-diol

Base Information

• Chemical Name: 2-({(2S,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: 627.778
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID70704886
• Mol file: 115250-39-0.mol

Synonyms:Tetrabenzyl-voglibose(TBV);DTXSID70704886;AKOS025402027;AC-3386;2-({(2S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexyl}amino)propane-1,3-diol

Chemical Property of 2-({(2S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexyl}amino)propane-1,3-diol

Chemical Property:

• Vapor Pressure: 6.73E-26mmHg at 25°C
• Refractive Index: 1.629
• Boiling Point: 784.1 °C at 760 mmHg
• PKA: 12.98±0.70(Predicted)
• Flash Point: 428 °C
• PSA: 109.64000
• Density: 1.24 g/cm³
• LogP: 4.79650
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 17
• Exact Mass: 627.31960277
• Heavy Atom Count: 46
• Complexity: 805

Purity/Quality:

99% ^*data from raw suppliers

Tetrabenzyl Voglibose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1(COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)NC(CO)CO
• Isomeric SMILES: C1C([C@@H](C([C@@H]([C@]1(COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)NC(CO)CO
• Uses: Tetrabenzyl-voglibose is a derivative of Voglibose which is an α-Glucosidase inhibitor used as an antidiabetic.

Technology Process of 2-({(2S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexyl}amino)propane-1,3-diol

There total 12 articles about 2-({(2S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexyl}amino)propane-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(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)

Guidance literature:

With sodium cyanoborohydride; In methanol; for 16h; Ambient temperature;

DOI:10.1021/jo00039a026

Reference yield:

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)

Guidance literature:

tetra-O-benzylvaliolamine; serinol; In methanol; at 20 ℃; for 1h;

With sodium cyanoborohydride; In methanol;

With hydrogenchloride; In methanol; water; pH=8.0;

Reference yield:

dihydroxyacetone (96-26-4,26776-70-5) + 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)

Guidance literature:

dihydroxyacetone; tetra-O-benzylvaliolamine; In methanol; at 20 - 30 ℃; for 0.5 - 1h;

With hydrogenchloride; sodium cyanoborohydride; In methanol; water; pH=~ 6.0; Product distribution / selectivity;

upstream raw materials:

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol

serinol

tetra-O-benzylvaliolamine

dihydroxyacetone

Downstream raw materials:

voglibose

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF 1,2,3,4-CYCLOHEXANETETROL DERIVATIVES". Page/Page column 19-20. . Retrieved 2008/06/13.