Phosphorous acid bis-(2-cyano-ethyl) ester (1S,2R,3R,4S,5S,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester

Base Information

• Chemical Name: Phosphorous acid bis-(2-cyano-ethyl) ester (1S,2R,3R,4S,5S,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester
• CAS No.: 109522-11-4
• Molecular Formula: C₄₅H₅₁N₆O₁₂P₃
• Molecular Weight: 960.854
• Mol file: 109522-11-4.mol

Synonyms:

Chemical Property of Phosphorous acid bis-(2-cyano-ethyl) ester (1S,2R,3R,4S,5S,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphorous acid bis-(2-cyano-ethyl) ester (1S,2R,3R,4S,5S,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester

There total 13 articles about Phosphorous acid bis-(2-cyano-ethyl) ester (1S,2R,3R,4S,5S,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-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:

(±)-2,3,6-tri-O-benzyl-myo-inositol (98906-30-0,104873-76-9,111466-07-0,114297-88-0,114297-91-5,114419-08-8,115184-71-9,115509-75-6,115509-76-7,118354-54-4,118354-55-5,128163-34-8,129706-80-5,136521-84-1,149713-88-2,149713-95-1) → Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester (109522-11-4,145842-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: EtN(iPr)2 / CH₂Cl₂

2: tetrazole / CH₂Cl₂

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/c39870001525

Reference yield:

(±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol (98906-25-3,114297-83-5,117307-15-0,142435-92-5,173828-64-3) → Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester (109522-11-4,145842-33-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / pyridine / 2 h

2: 91 percent / concd. HCl / methanol; tetrahydrofuran / Ambient temperature

3: 80 percent / pyridine / 3 h

4: 70 percent / triflic acid / cyclohexane; CH₂Cl₂ / 12 h / Ambient temperature

5: 86 percent / K₂CO₃ / methanol; CH₂Cl₂ / 24 h / Ambient temperature

6: 1H-tetrazole / acetonitrile; CH₂Cl₂ / Ambient temperature

With 1H-tetrazole; hydrogenchloride; trifluorormethanesulfonic acid; potassium carbonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; cyclohexane; acetonitrile;

DOI:10.1016/S0040-4020(97)00714-X

Reference yield:

benzoyl chloride (98-88-4) → Phosphorous acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphanyloxy]-cyclohexyl ester (109522-11-4,145842-33-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / pyridine / 2 h

2: 91 percent / concd. HCl / methanol; tetrahydrofuran / Ambient temperature

3: 80 percent / pyridine / 3 h

4: 70 percent / triflic acid / cyclohexane; CH₂Cl₂ / 12 h / Ambient temperature

5: 86 percent / K₂CO₃ / methanol; CH₂Cl₂ / 24 h / Ambient temperature

6: 1H-tetrazole / acetonitrile; CH₂Cl₂ / Ambient temperature

With 1H-tetrazole; hydrogenchloride; trifluorormethanesulfonic acid; potassium carbonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; cyclohexane; acetonitrile;

DOI:10.1016/S0040-4020(97)00714-X

upstream raw materials:

Diisopropyl-phosphoramidous acid 2-cyano-ethyl ester (1R,2S,3R,4R,5S,6R)-2,3,5-tris-benzyloxy-4,6-bis-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-cyclohexyl ester

3-Hydroxypropionitrile

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

benzoyl chloride

Downstream raw materials:

1D-2,5,6-Tri-O-benzyl-myo-inositol 1,3,4-tris

Phosphoric acid bis-(2-cyano-ethyl) ester (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-[bis-(2-cyano-ethoxy)-phosphoryloxy]-cyclohexyl ester