Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester

Base Information

• Chemical Name: Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester
• CAS No.: 1055041-92-3
• Molecular Formula: C₅₆H₆₆NO₉P
• Molecular Weight: 928.115

Synonyms:Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester

Chemical Property of Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester

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Technology Process of Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester

There total 16 articles about Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-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:

quebrachitol (642-38-6) → Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester (1055041-92-3)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 91 percent / CSA / dimethylformamide / 5 h / 20 - 60 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

3.1: 42 g / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

4.1: CSA / dimethylformamide / 4 h / 80 °C

5.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

6.1: 2.46 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

7.1: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -60 °C

8.1: 2.15 g / NaBH₄ / methanol / 1 h / 5 °C

9.1: NaH; PMBCl / Bu₄NI / dimethylformamide / 4 h / 0 °C

10.1: 2.1 g / AcCl; MeOH / CH₂Cl₂

11.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

12.1: 1.6 g / conc. HCl / methanol

13.1: Bu₂SnO / toluene / 2 h / Heating

13.2: CsF / dimethylformamide / 18 h / 20 °C

14.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

15.1: DABCO / RhCl(PPh₃)3 / ethanol / 6 h / Heating

16.1: 1.93 g / aq. HCl / acetone / 0.5 h / Heating

17.1: diisopropylammonium tetrazolide

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; N,N-diisopropylamine tetrazolide; boron tribromide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; RhCl(PPh₃)3; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Cyclization / 2.1: mesylation / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Etherification / 6.1: Reduction / 7.1: Swern oxidation / 8.1: Reduction / 9.1: Etherification / 10.1: Hydrolysis / 11.1: Etherification / 12.1: Hydrolysis / 13.1: Cyclization / 13.2: Substitution / 14.1: Etherification / 15.1: Isomerization / 16.1: Hydrolysis / 17.1: phosphitylation;

DOI:10.1021/ol991188y

Reference yield:

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6) → Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester (1055041-92-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: 42 g / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

3.1: CSA / dimethylformamide / 4 h / 80 °C

4.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

5.1: 2.46 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

6.1: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -60 °C

7.1: 2.15 g / NaBH₄ / methanol / 1 h / 5 °C

8.1: NaH; PMBCl / Bu₄NI / dimethylformamide / 4 h / 0 °C

9.1: 2.1 g / AcCl; MeOH / CH₂Cl₂

10.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

11.1: 1.6 g / conc. HCl / methanol

12.1: Bu₂SnO / toluene / 2 h / Heating

12.2: CsF / dimethylformamide / 18 h / 20 °C

13.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

14.1: DABCO / RhCl(PPh₃)3 / ethanol / 6 h / Heating

15.1: 1.93 g / aq. HCl / acetone / 0.5 h / Heating

16.1: diisopropylammonium tetrazolide

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; N,N-diisopropylamine tetrazolide; boron tribromide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; RhCl(PPh₃)3; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: mesylation / 2.1: Ring cleavage / 3.1: Cyclization / 4.1: Etherification / 5.1: Reduction / 6.1: Swern oxidation / 7.1: Reduction / 8.1: Etherification / 9.1: Hydrolysis / 10.1: Etherification / 11.1: Hydrolysis / 12.1: Cyclization / 12.2: Substitution / 13.1: Etherification / 14.1: Isomerization / 15.1: Hydrolysis / 16.1: phosphitylation;

DOI:10.1021/ol991188y

Reference yield:

(1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol (116180-58-6) → Diisopropyl-phosphoramidous acid benzyl ester (1S,2R,3S,4S,5R,6R)-2,3,6-tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester (1055041-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Bu₂SnO / toluene / 2 h / Heating

1.2: CsF / dimethylformamide / 18 h / 20 °C

2.1: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

3.1: DABCO / RhCl(PPh₃)3 / ethanol / 6 h / Heating

4.1: 1.93 g / aq. HCl / acetone / 0.5 h / Heating

5.1: diisopropylammonium tetrazolide

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; N,N-diisopropylamine tetrazolide; sodium hydride; di(n-butyl)tin oxide; RhCl(PPh₃)3; tetra-(n-butyl)ammonium iodide; In ethanol; N,N-dimethyl-formamide; acetone; toluene; 1.1: Cyclization / 1.2: Substitution / 2.1: Etherification / 3.1: Isomerization / 4.1: Hydrolysis / 5.1: phosphitylation;

DOI:10.1021/ol991188y

upstream raw materials:

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

(1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

quebrachitol

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

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