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

Base Information

• Chemical Name: (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester
• CAS No.: 120444-20-4
• Molecular Formula: C₄₄H₄₇FO₈
• Molecular Weight: 722.851
• Mol file: 120444-20-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-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: 34.0%

(1S)-(-)-camphanic chloride (39637-74-6) + (1S,2S,3R,4S,5R,6R)-2,3,4,5-Tetrakis-benzyloxy-6-fluoro-cyclohexanol (85747-85-9,97335-94-9,97335-95-0,97335-96-1,120444-19-1,120444-21-5,120444-22-6,120444-23-7,129707-22-8) → (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester (120444-20-4) + (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester (120401-18-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; 0 deg C to RT, RT, 24 h;

DOI:10.1016/S0008-6215(98)00146-3

Reference yield: 25.0%

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3R,5R)-2,3,4,5-tetrakis-benzyloxy-6-hydroxy-cyclohexyl ester → (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester (120444-20-4) + (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester (120401-18-5)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In toluene; at 70 - 80 ℃; for 2h;

DOI:10.1016/S0008-6215(98)00146-3

Reference yield:

rac-1,4,5,6-tetra-O-benzyl-myo-inositol (26276-99-3) → (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,3S,4S,5R,6S)-2,3,4,5-tetrakis-benzyloxy-6-fluoro-cyclohexyl ester (120444-20-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: diethylaminosulphur trifluoride / toluene / 80 °C

3: NaOH

4: Et₃N, DMAP / CH₂Cl₂

With pyridine; dmap; sodium hydroxide; diethylamino-sulfur trifluoride; triethylamine; In dichloromethane; toluene;

DOI:10.1039/c39880001301

upstream raw materials:

(1S)-(-)-camphanic chloride

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

rac-1,4,5,6-tetra-O-benzyl-myo-inositol

(+/-)-1-O-benzoyl-3,4,5,6-tetra-O-benzyl-myo-inositol

Downstream raw materials:

(-)-1D-3,4,5,6-Tetra-O-benzyl-1-deoxy-1-fluoro-myo-inositol

D-3,4,5,6-tetra-O-benzyl-1,2-dideoxy-1,2-difluoro-myo-inositol

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