(1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^0,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Base Information

• Chemical Name: (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^0,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS No.: 403806-10-0
• Molecular Formula: C₃₈H₅₁BO₄
• Molecular Weight: 582.632
• Mol file: 403806-10-0.mol

Synonyms:(1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^0,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property of (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^0,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^0,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester

There total 4 articles about (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.0^0,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)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:

(-)-8-phenylmenthol (65253-04-5) → (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.00,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (403806-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / 4-dimethylaminopyridine; DCC / CH₂Cl₂ / -78 - 20 °C

2.1: CuBr*SMe₂ / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

2.2: diethyl ether; tetrahydrofuran / 1.5 h / -78 °C

2.3: HMPA / tetrahydrofuran; diethyl ether / 2 h / 0 °C

3.1: 511 mg / NH₄Cl / diethyl ether; H₂O; tetrahydrofuran / 0.5 h / 20 °C

With dmap; copper(I) bromide dimethylsulfide complex; ammonium chloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1021/jo049773m

Reference yield:

(-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol (31503-17-0) + methyllithium (917-54-4) + (-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl tetrolate (169136-81-6) + diisopropyl (iodomethyl)boronate (167967-38-6) → (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.00,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (403806-10-0)

Guidance literature:

methyllithium; (-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl tetrolate; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether;

diisopropyl (iodomethyl)boronate; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; diethyl ether; for 2h; cooling;

(-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol; In tetrahydrofuran; diethyl ether; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/ja016391e

Reference yield:

(-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol (31503-17-0) + C28H45BO4 → (1R,2R,3R,4S)-3-methyl-2-(1,10,10-trimethyl-2-phenyl-3,5-dioxa-4-boratricyclo[5.2.1.00,0]dec-4-ylmethyl)but-2-enoic acid (1R,2S,3R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester (403806-10-0)

Guidance literature:

With ammonium chloride; In tetrahydrofuran; diethyl ether; water; at 20 ℃; for 0.5h;

DOI:10.1021/jo049773m

upstream raw materials:

(-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol

methyllithium

(-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl tetrolate

diisopropyl (iodomethyl)boronate