(1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

Base Information

• Chemical Name: (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester
• CAS No.: 134039-22-8
• Molecular Formula: C₅₂H₅₆O₁₀
• Molecular Weight: 841.011

Synonyms:

Chemical Property of (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

There total 20 articles about (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(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: 46.0%

(-)-camphanic acid chloride (39637-74-6,104530-16-7) + (1R,2R,3S,4R,5R,6R)-2,3,5,6-Tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexanol (134039-21-7,134107-72-5,134107-73-6,141040-52-0) → (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester (134039-22-8,134107-71-4) + (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester (134039-22-8,134107-71-4)

Guidance literature:

DOI:10.1016/S0040-4039(00)92129-4

Reference yield: 46.0%

(-)-camphanic acid chloride (39637-74-6,104530-16-7) + (1R,2R,3S,4R,5R,6R)-2,3,5,6-Tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexanol (134039-21-7,134107-72-5,134107-73-6,141040-52-0) → (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester (134039-22-8,134107-71-4) + (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2S,3R,4S,5S,6S)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester (134039-22-8,134107-71-4)

Guidance literature:

DOI:10.1016/S0040-4039(00)92129-4

Reference yield:

1,2:4,5-dicyclohexylidene-myo-inositol (34361-60-9,55123-24-5,55123-26-7,62012-78-6,104873-71-4) → (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester (134039-22-8,134107-71-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 68 percent / BaO/Ba(OH)2 / dimethylformamide / 72 h / 20 °C

2: 1) NaH

3: HOCH₂CH₂OH / CH₂Cl₂

4: 1) NaH

5: 0.05N HCl / methanol

6: 1) NaH

7: 1,5-cyclooctadiene-bis-IrPF₆, activated with H₂ / 1,2-dichloro-ethane

8: 0.1 HCl / CH₂Cl₂; methanol

9: 43 percent

With hydrogenchloride; barium dihydroxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen; sodium hydride; ethylene glycol; barium(II) oxide; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92129-4

upstream raw materials:

(-)-camphanic acid chloride

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

1,2:4,5-dicyclohexylidene-myo-inositol

benzyl bromide

Downstream raw materials:

Methyl-phosphonic acid benzyl ester (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

((S)-3,4-Dihydroxy-butyl)-phosphonic acid benzyl ester (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-phosphonic acid benzyl ester (1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

Hexadecanoic acid (S)-3-[benzyloxy-((1S,2R,3R,4S,5S,6R)-2,3,5,6-tetrakis-benzyloxy-4-hydroxy-cyclohexyloxy)-phosphoryl]-1-hexadecanoyloxymethyl-propyl ester

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