(+)-Pinaneborane

Base Information

• Chemical Name: (+)-Pinaneborane
• CAS No.: 90084-43-8
• Molecular Formula: C10H17 B O2
• Molecular Weight: 180.05
• Mol file: 90084-43-8.mol

Synonyms:4,6-Methano-1,3,2-benzodioxaborole,hexahydro-3a,5,5-trimethyl-, (3aS,4R,6R,7aR)- (9CI);4,6-Methano-1,3,2-benzodioxaborole, hexahydro-3a,5,5-trimethyl-, [3aS-(3aa,4b,6b,7aa)]-

Chemical Property of (+)-Pinaneborane

Chemical Property:

• PSA: 18.46000
• LogP: 1.49300
• Storage Temp.: Refrigerated.
• Solubility.: Chloroform (Slightly), Toluene (Sparingly)

Purity/Quality:

97% ^*data from raw suppliers

(+)-PinanediolBorane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (+)-Pinanediol Borane is a chiral catalyst used in the synthesis of N-acyl L-amino acids.

Technology Process of (+)-Pinaneborane

There total 2 articles about (+)-Pinaneborane 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: 78.0%

pinanediol (18680-27-8) + dimethyl sulfide borane (13292-87-0) → (3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-43-8)

Guidance literature:

In tetrahydrofuran; A soln. of reagents in THF was stirred under Ar at 0°C, then at 20-25°C for 2 H;; distilled; elem. anal.;;

Reference yield:

pinanediol (18680-27-8) → (3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-43-8)

Guidance literature:

With dimethylsulfide borane complex; In 1,4-dioxane;

Reference yield: 97.0%

1-(tert-butyl) 2-methyl (2R,3R,Z)-3-allyl-4-(2-(benzyloxy)-2-oxoethylidene)pyrrolidine-1,2-dicarboxylate + (3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-43-8) → 1-(tert-butyl) 2-methyl (2R,3R,Z)-4-(2-(benzyloxy)-2-oxoethylidene)-3-(3-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)propyl)pyrrolidine-1,2-dicarboxylate

Guidance literature:

(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane; In dichloromethane; at 25 ℃; for 0.333333h; Inert atmosphere;

1-(tert-butyl) 2-methyl (2R,3R,Z)-3-allyl-4-(2-(benzyloxy)-2-oxoethylidene)pyrrolidine-1,2-dicarboxylate; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.1c00258

upstream raw materials:

pinanediol

dimethyl sulfide borane

Downstream raw materials:

(dimethylphenylsilyl)((+)-pinanediolato)borane

(+)-pinanediol 3-benzyloxypropaneboronate

(3aS,4S,6S,7aR)-2-(3-bromopropyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole