Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester

Base Information

• Chemical Name: Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester
• CAS No.: 556053-49-7
• Molecular Formula: C₆₉H₁₀₅NO₁₆P₂
• Molecular Weight: 1266.54

Synonyms:Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester

Chemical Property of Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester

Chemical Property:

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Technology Process of Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester

There total 10 articles about Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} 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: 82.0%

bicyclohexyl-4,4'-dicarboxylic acid 4-benzyl ester + (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (556031-71-1) → Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester (556053-49-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1002/1521-3773(20021115)41:22<4289::AID-ANIE4289>3.0.CO;2-4

Reference yield:

n-butyl N-acetyl-β-glucosaminide (94536-61-5) → Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester (556053-49-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / TsOH / dimethylformamide

2: 80 percent / N₂H₄ / ethanol / 130 °C

3: DCC; 4-pyrrolidino-pyridine / CH₂Cl₂

4: aq. AcOH

5: 82 percent / DCC; DMAP

With dmap; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; hydrazine; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20021115)41:22<4289::AID-ANIE4289>3.0.CO;2-4

Reference yield:

n-butyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (155197-37-8) → Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester (556053-49-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / NaOMe / methanol

2: 82 percent / TsOH / dimethylformamide

3: 80 percent / N₂H₄ / ethanol / 130 °C

4: DCC; 4-pyrrolidino-pyridine / CH₂Cl₂

5: aq. AcOH

6: 82 percent / DCC; DMAP

With dmap; sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; hydrazine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20021115)41:22<4289::AID-ANIE4289>3.0.CO;2-4

upstream raw materials:

(R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

n-butyl N-acetyl-β-glucosaminide

n-butyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

(R)-3-hydroxyoctanoic acid t-butyl ester

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