(3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide

Base Information

• Chemical Name: (3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide
• CAS No.: 140391-24-8
• Molecular Formula: C12H22NO12P
• Molecular Weight: 403.276341
• Mol file: 140391-24-8.mol

Synonyms:CHEBI:58891;6-(alpha-D-glucosaminyl)-1D-myo-inositol 1,2-cyclic phosphate zwitterion;6-(2-azaniumyl-2-deoxy-beta-D-glucopyranosyl)-1D-myo-inositol 1,2-phosphate;(3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide

Chemical Property of (3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide

Chemical Property:

• PSA: 231.43000
• LogP: -4.18110
• XLogP3: -5.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 403.08796213
• Heavy Atom Count: 26
• Complexity: 558

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC2C(C(C(C3C2OP(=O)(O3)[O-])O)O)O)[NH3+])O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]3[C@H]2OP(=O)(O3)[O-])O)O)O)[NH3+])O)O)O

Technology Process of (3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide

There total 8 articles about (3aS,4R,5S,6S,7R,7aR)-4-[(2-azaniumyl-2-deoxy-alpha-D-glucopyranosyl)oxy]-5,6,7-trihydroxyhexahydro-1,3,2-benzodioxaphosphol-2-olate 2-oxide 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: 20.0%

6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (129210-15-7) → 6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate (140391-24-8)

Guidance literature:

With 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide methyl-p-toluenesulfonate; In water;

DOI:10.1021/jo00035a015

Reference yield:

6-O-(2-Azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-(dibenzylphosphono)-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol → 6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate (140391-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) H₂, 2) 50percent aq. HOAc / 1) 10percent Pd-C / 1) aq. EtOH, HOAc, 48 psig, 24 h, 2) 25 deg C, 3 h

2: 20 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide methyl-p-toluenesulfonate / H₂O

With 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide methyl-p-toluenesulfonate; hydrogen; acetic acid; palladium on activated charcoal; In water;

DOI:10.1021/jo00035a015

Reference yield:

(3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ5-benzo[1,3,2]dioxaphosphol-2-ol (452915-75-2) → 6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate (140391-24-8)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -33 ℃; for 0.0166667h;

DOI:10.1016/S0040-4020(02)00359-9

upstream raw materials:

6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate

O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-1,5,6-tri-O-benzyl-L-myo-inositol

(3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol

6-O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,4,5-tri-O-benzyl-D-myo-inositol

Refernces

• 1、 Dietrich, Hansjoerg,Espinosa, Juan Felix,Chiara, Jose Luis,Jimenez-Barbero, Jesus,Leon, Yolanda,Varela-Nieto, Isabel,Mato, Jose-Maria,Cano, Felix H.,Foces-Foces, Concepcion,Martin-Lomas, Manuel. "Glycosyl inositol derivatives related to inositolphosphoglycan mediators: Synthesis, structure, and biological activity". . p. 320 - 336. Retrieved 2007/10/03.
• 2、 Plourde,D'Alarcao,Saltiel. "Synthesis and characterization of an insulin-mimetic disaccharide". . p. 2606 - 2610. Retrieved 2007/10/02.