[(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrahydroxy-6-phosphonooxycyclohexyl] dihydrogen phosphate

Base Information

• Chemical Name: [(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrahydroxy-6-phosphonooxycyclohexyl] dihydrogen phosphate
• CAS No.: 69256-53-7
• Molecular Formula: C₆H₁₄O₁₂P₂
• Molecular Weight: 340.117
• Nikkaji Number: J2.516.424E
• Mol file: 69256-53-7.mol

Synonyms:D-myo-Inositol, 3,4-bis(dihydrogen phosphate);69256-53-7;SCHEMBL8994052;[(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrahydroxy-6-phosphonooxycyclohexyl] dihydrogen phosphate

Chemical Property of [(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrahydroxy-6-phosphonooxycyclohexyl] dihydrogen phosphate

Chemical Property:

• Vapor Pressure: 7.85E-22mmHg at 25°C
• Boiling Point: 686.8°Cat760mmHg
• Flash Point: 369.1°C
• Density: 2.15g/cm³
• XLogP3: -5.9
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 4
• Exact Mass: 339.99604987
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1(C(C(C(C(C1O)OP(=O)(O)O)OP(=O)(O)O)O)O)O
• Isomeric SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)OP(=O)(O)O)O)O)O

Technology Process of [(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrahydroxy-6-phosphonooxycyclohexyl] dihydrogen phosphate

There total 9 articles about [(1R,2S,3R,4R,5R,6R)-2,3,4,5-tetrahydroxy-6-phosphonooxycyclohexyl] dihydrogen phosphate 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:

(+/-)-1,4-Di-O-benzyl-myo-inositol 5,6-bis(dibenzyl phosphate) → (+/-)-myo-inositol 4,5-bisphosphate (23410-61-9,41613-00-7,41613-01-8,69256-53-7,69256-54-8,74465-15-9,74465-17-1,93060-87-8,95120-19-7,109584-32-9,131321-70-5,131321-71-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 12h; under 760 Torr; Yield given;

Reference yield:

(5S,6S)-5,6-Bis-(2-methoxy-ethoxymethoxy)-cyclohex-2-ene-1,4-dione (130659-82-4) → (+/-)-myo-inositol 4,5-bisphosphate (23410-61-9,41613-00-7,41613-01-8,69256-53-7,69256-54-8,74465-15-9,74465-17-1,93060-87-8,95120-19-7,109584-32-9,131321-70-5,131321-71-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄, CeCl₃

2: 95 percent / NaH

3: 96 percent / OsO₄, N-methylmorpholine-N-oxide

4: NaH

5: 6 M HCl / tetrahydrofuran / 20 °C

6: BuLi / tetrahydrofuran

7: H₂ / Pd/C

With hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; hydrogen; sodium hydride; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)97419-7

Reference yield:

(1R,2S,3S,4R,5R,6S)-3,6-Bis-benzyloxy-4,5-bis-(2-methoxy-ethoxymethoxy)-cyclohexane-1,2-diol (129662-36-8,130792-09-5) → (+/-)-myo-inositol 4,5-bisphosphate (23410-61-9,41613-00-7,41613-01-8,69256-53-7,69256-54-8,74465-15-9,74465-17-1,93060-87-8,95120-19-7,109584-32-9,131321-70-5,131321-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH

2: 6 M HCl / tetrahydrofuran / 20 °C

3: BuLi / tetrahydrofuran

4: H₂ / Pd/C

With hydrogenchloride; n-butyllithium; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)97419-7

upstream raw materials:

(+/-)-1,2,3,4-Tetra-O-benzyl-myo-inositol 5,6-bis(dinbenzyl phosphate)

(±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol

(5S,6S)-5,6-Bis-(2-methoxy-ethoxymethoxy)-cyclohex-2-ene-1,4-dione

C₂₈H₃₈O₈

Refernces

• 1、 Carless, Howard A. J.,Busia, Kofi. "Total synthesis of myo-inositol polyphosphates from benzene via conduritol B derivatives". . p. 3449 - 3452. Retrieved 2007/10/02.