{(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester

Base Information

• Chemical Name: {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester
• CAS No.: 444902-91-4
• Molecular Formula: C₅₇H₅₉O₁₀P
• Molecular Weight: 935.063

Synonyms:{(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester

Chemical Property of {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester

There total 10 articles about {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl 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: 48.0%

Dibenzyl phosphite (17176-77-1) + (1R,2R,3S,4R,5R,6R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexanecarbaldehyde → {(R)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester (444902-92-5) + {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester (444902-91-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(02)00354-4

Reference yield:

p-methoxybenzyl chloride (824-94-2) → {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester (444902-91-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Bu₂SnO / toluene / Heating

1.2: CsF / dimethylformamide / 20 °C

2.1: NaH / dimethylformamide / 0 - 20 °C

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

3.2: HCl / acetone / Heating

4.1: Dess-Martin periodinane / CH₂Cl₂

5.1: 48 percent / BuLi / tetrahydrofuran / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; RhCl(PPh₃)3; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(02)00354-4

Reference yield:

1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol (291313-64-9) → {(S)-Hydroxy-[(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl]-methyl}-phosphonic acid dibenzyl ester (444902-91-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

2.1: AcCl / CH₂Cl₂; methanol / 20 °C

3.1: NaH / dimethylformamide / 0 - 20 °C

4.1: AcCl / methanol / 20 °C

5.1: Bu₂SnO / toluene / Heating

5.2: CsF / dimethylformamide / 20 °C

6.1: NaH / dimethylformamide / 0 - 20 °C

7.1: DABCO / RhCl(PPh₃)3 / ethanol / Heating

7.2: HCl / acetone / Heating

8.1: Dess-Martin periodinane / CH₂Cl₂

9.1: 48 percent / BuLi / tetrahydrofuran / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; acetyl chloride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(02)00354-4

upstream raw materials:

Dibenzyl phosphite

p-methoxybenzyl chloride

1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-hydroxymethyl-myo-inositol

Downstream raw materials:

((S)-Hydroxy-{(1R,2R,3S,4R,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-[benzyloxy-((R)-2-methoxy-3-octadecyloxy-propoxy)-phosphoryloxy]-cyclohexyl}-methyl)-phosphonic acid dibenzyl ester

[(S)-Hydroxy-((1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxy-cyclohexyl)-methyl]-phosphonic acid dibenzyl ester

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