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

Base Information

• Chemical Name: Phosphoric acid dibenzyl ester (1S,2R,3R,4R,5R,6S)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-fluoro-cyclohexyl ester
• CAS No.: 127437-38-1
• Molecular Formula: C₆₂H₆₂FO₁₄P₃
• Molecular Weight: 1143.09
• Mol file: 127437-38-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol (114218-23-4,114297-87-9,114298-50-9) → Phosphoric acid dibenzyl ester (1S,2R,3R,4R,5R,6S)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-fluoro-cyclohexyl ester (127437-38-1,145681-20-5,149198-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / DAST / CH₂Cl₂ / 0 °C

2: 91 percent / DABCO / Wilkinson's catalyst / ethanol

3: 83 percent / H₃O+ / methanol

4: 1.) NaH / 1.) DMF, 0 deg C

With 1,4-diaza-bicyclo[2.2.2]octane; oxonium; sodium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; Wilkinson's catalyst; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(01)80578-5

Reference yield:

(3aR,4R,5S,6R,7R,7aS)-5-Allyloxy-4,7-bis-benzyloxy-6-fluoro-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (127414-68-0) → Phosphoric acid dibenzyl ester (1S,2R,3R,4R,5R,6S)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-fluoro-cyclohexyl ester (127437-38-1,145681-20-5,149198-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / DABCO / Wilkinson's catalyst / ethanol

2: 83 percent / H₃O+ / methanol

3: 1.) NaH / 1.) DMF, 0 deg C

With 1,4-diaza-bicyclo[2.2.2]octane; oxonium; sodium hydride; Wilkinson's catalyst; In methanol; ethanol;

DOI:10.1016/S0040-4039(01)80578-5

Reference yield:

1D-(-)-1-O-Allyl-3,6-di-O-benzyl-isopropylidene-scyllo-inositol (181783-26-6) → Phosphoric acid dibenzyl ester (1S,2R,3R,4R,5R,6S)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-fluoro-cyclohexyl ester (127437-38-1,145681-20-5,149198-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: DAST / CH₂Cl₂ / 0 °C

2: 91 percent / DABCO / Wilkinson's catalyst / ethanol

3: 83 percent / H₃O+ / methanol

4: 1.) NaH / 1.) DMF, 0 deg C

With 1,4-diaza-bicyclo[2.2.2]octane; oxonium; sodium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; Wilkinson's catalyst; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(01)80578-5

upstream raw materials:

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

2-deoxy-2-fluoro-1,4-di-O-benzyl-scyllo-inositol

(3aR,4R,5S,6R,7R,7aS)-5-Allyloxy-4,7-bis-benzyloxy-6-fluoro-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

(3aS,4R,5S,6S,7R,7aR)-4,7-Bis-benzyloxy-5-fluoro-2,2-dimethyl-6-[((E)-propenyl)oxy]-hexahydro-benzo[1,3]dioxole

Downstream raw materials:

(+/-)-2-deoxy-2-fluoro-scyllo-inositol 1,4,5-trisphosphate