Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-{(S)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Base Information

• Chemical Name: Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-{(S)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
• CAS No.: 118964-45-7
• Molecular Formula: C₇₄H₈₃N₂O₁₁P
• Molecular Weight: 1207.45

Synonyms:

Chemical Property of Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-{(S)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-{(S)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

There total 17 articles about Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-{(S)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl 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: 88.0%

2,5-di-O-benzyl-β-D-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol (118964-44-6) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → Diisopropyl-phosphoramidous acid (2R,3R,4R)-4-benzyloxy-2-benzyloxymethyl-5-{(2S,3R,4R)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (118964-45-7,119066-00-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)97590-8

Reference yield:

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → Diisopropyl-phosphoramidous acid (2R,3R,4R)-4-benzyloxy-2-benzyloxymethyl-5-{(2S,3R,4R)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (118964-45-7,119066-00-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 90 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature

2: 70percent aq. acetic acid / 6 h / 80 °C

3: pyridine, DMAP / CH₂Cl₂ / 0.5 h

4: HCl-gas / CH₂Cl₂ / 18 h / 0 °C

5: CH₂Cl₂ / 3 h / Ambient temperature

6: sodium methoxide / methanol / 3 h / Ambient temperature

7: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / 18 h / Ambient temperature

8: trimethylsilyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

9: silver perchlorate, molecular sieve / acetonitrile / 4 h / -40 °C

10: sodium methoxide / methanol / 2 h / Ambient temperature

11: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

12: 90 percent / lithium triethylborohydride / tetrakis(triphenylphosphine)palladium⁽⁰⁾, triphenylphosphine / dioxane; tetrahydrofuran / 1 h / Heating

13: 86 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

14: 88 percent / diisopropylethylamine / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; chloro-trimethyl-silane; molecular sieve; sodium methylate; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)97590-8

Reference yield:

β-5-O-allyl-1-O-methyl-2,3-O,O-isopropylidene-D-ribofuranoside (114488-50-5) → Diisopropyl-phosphoramidous acid (2R,3R,4R)-4-benzyloxy-2-benzyloxymethyl-5-{(2S,3R,4R)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (118964-45-7,119066-00-1)

Guidance literature:

Multi-step reaction with 11 steps

1: water, sulfuric acid / methanol / 2 h / Heating

2: 94 percent / zinc chloride / 0.25 h / Ambient temperature

3: 91 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

4: mercury(II)chloride, mercury(II)oxide / acetone; H₂O / 2 h / Ambient temperature

5: sodium borohydride / methanol

6: silver perchlorate, molecular sieve / acetonitrile / 4 h / -40 °C

7: sodium methoxide / methanol / 2 h / Ambient temperature

8: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

9: 90 percent / lithium triethylborohydride / tetrakis(triphenylphosphine)palladium⁽⁰⁾, triphenylphosphine / dioxane; tetrahydrofuran / 1 h / Heating

10: 86 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

11: 88 percent / diisopropylethylamine / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; molecular sieve; sulfuric acid; water; sodium methylate; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)97590-8

upstream raw materials:

2,5-di-O-benzyl-β-D-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

β-5-O-allyl-1-O-methyl-2,3-O,O-isopropylidene-D-ribofuranoside

(3aR,5R,6R,6aR)-6-Allyloxy-5-benzyloxymethyl-2-methoxy-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxole

Downstream raw materials:

C₁₁₈H₁₂₄NO₂₃P

C₁₁₈H₁₂₄NO₂₃P

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