(1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

Base Information

• Chemical Name: (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester
• CAS No.: 114218-18-7
• Molecular Formula: C₄₀H₄₆O₉
• Molecular Weight: 670.8
• Mol file: 114218-18-7.mol

Synonyms:

Chemical Property of (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl 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 (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

There total 8 articles about (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl 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: 80.0%

1D-2,3,6-Tri-O-benzyl-4,5-O-isopropylidene-myo-inositol (125474-19-3) + (-)-camphanic acid chloride (39637-74-6,104530-16-7) → 1D-2,3,6-Tri-O-benzyl-4,5-O-isopropylidene-myo-inositol (+)-ω-camphanate (114218-18-7,120143-58-0,120143-99-9,125474-18-2,125474-24-0,141040-42-8) + (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (114218-18-7,120143-58-0,120143-99-9,125474-18-2,125474-24-0,141040-42-8)

Guidance literature:

With pyridine;

DOI:10.1016/S0008-6215(00)90497-X

Reference yield: 80.0%

1D-2,3,6-Tri-O-benzyl-4,5-O-isopropylidene-myo-inositol (125474-19-3) + (-)-camphanic acid chloride (39637-74-6,104530-16-7) → 1D-2,3,6-Tri-O-benzyl-4,5-O-isopropylidene-myo-inositol (+)-ω-camphanate (114218-18-7,120143-58-0,120143-99-9,125474-18-2,125474-24-0,141040-42-8) + (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (114218-18-7,120143-58-0,120143-99-9,125474-18-2,125474-24-0,141040-42-8)

Guidance literature:

With pyridine;

DOI:10.1016/S0008-6215(00)90497-X

Reference yield:

(+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol (111446-91-4,114297-90-4,114297-93-7,120143-57-9,120143-61-5,120143-62-6,125474-19-3,149713-81-5,149713-82-6) → (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5S,6S,7R,7aS)-4,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (114218-18-7,120143-58-0,120143-99-9,125474-18-2,125474-24-0,141040-42-8)

Guidance literature:

Multi-step reaction with 3 steps

2: NaOH / methanol

3: pyridine

With pyridine; sodium hydroxide; In methanol;

DOI:10.1016/S0008-6215(00)90497-X

upstream raw materials:

(-)-camphanic acid chloride

(+/-)-1,6-O-isopropylidene-2,4,5-tri-O-benzyl-myo-inositol

(1S)-(-)-camphanic chloride

(+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol

Downstream raw materials:

(3aR,4R,5R,6R,7S,7aR)-4,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol

(-)-1L-2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol

(+)-1L-2,5,6-tri-O-benzyl-myo-inositol

(3aR,4R,5S,6R,7S,7aR)-4,6,7-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol