Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

Base Information

Chemical Name:Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester
CAS No.:115432-20-7
Molecular Formula:C₇₆H₇₆O₁₈P₄
Molecular Weight:1401.32
Hs Code.:

Synonyms:Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

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Chemical Property of Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

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Technology Process of Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

There total 26 articles about Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester 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: 27.0%

: 990-91-0
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

: 115432-20-7,125412-35-3,141040-65-5
Phosphoric acid dibenzyl ester (1S,2S,3R,4R,5R,6R)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

Guidance literature:: With n-butyllithium; at -40 ℃;
DOI:10.1016/0040-4039(90)80032-H

Reference yield:

: C₇₆H₇₆O₁₄P₄

: 115432-20-7,125412-35-3,141040-65-5
octabenzyl (±)-2,3,5,6-(1,4-di-O-benzyl-myo-inosityl)tetrakisphosphate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; at -40 - 0 ℃; for 5h; Inert atmosphere;
DOI:10.1002/cmdc.201000421

Reference yield:

: 18929-63-0
methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

: 115432-20-7
Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,5-bis-benzyloxy-3,4,6-tris-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 37 percent / n-Bu₄NHSO₄, aq. NaOH / CH₂Cl₂ / 48 h / Heating

2: 76 percent / NaH / dimethylformamide / 2 h / 50 °C

3: 77 percent / DIBAL-H / CH₂Cl₂ / 1 h / -40 °C

4: 1.) (COCl)2, DMSO, 2.) K₂CO₃ / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) MeCN, reflux, overnight

5: 1.) Hg(OAc)2, 2.) aq. NaCl / 1.) Me₂CO, H₂O, 45 min, 2.) room temperature, 24 h

6: 59 percent / NaBH(OAc)3, glacial AcOH / acetonitrile / 0.75 h / Ambient temperature

7: 90 percent / NaOH / methanol / 2 h / Heating

8: 85 percent / TsOH / acetone / 48 h / Ambient temperature

9: 80 percent / NaH / dimethylformamide / 2 h / Ambient temperature

10: 77 percent / TsOH / acetone; H₂O / 72 h / Ambient temperature

11: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, room temperature, 1 h, 2.) 0 deg C, 30 min; room temperature, 30 min

12: 64 percent / (NH₄)2Ce(NO₃)2 / acetonitrile; H₂O / 2 h / Ambient temperature

13: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, room temperature, 1 h, 2.) 0 deg C, 30 min; room temperature, 30 min

With 1H-tetrazole; sodium hydroxide; oxalyl dichloride; (NH₄)2Ce(NO₃)2; mercury(II) diacetate; tetra(n-butyl)ammonium hydrogensulfate; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; sodium chloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo951057k