445469-32-9

Basic information

• Product Name: (1R,2S,3R,4S,5R)-[2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-5-hydroxymethylcyclohexyl]carbamic acid tert-butyl ester
• Synonyms: (1R,2S,3R,4S,5R)-[2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-5-hydroxymethylcyclohexyl]carbamic acid tert-butyl ester
• CAS NO: 445469-32-9
• Molecular Weight: 620.106
• Mol File: 445469-32-9.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S,3R,4S,5R)-[2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-5-hydroxymethylcyclohexyl]carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3R,4S,5R)-[2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-5-hydroxymethylcyclohexyl]carbamic acid tert-butyl ester(445469-32-9)
• EPA Substance Registry System: (1R,2S,3R,4S,5R)-[2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-5-hydroxymethylcyclohexyl]carbamic acid tert-butyl ester(445469-32-9)

Safety Data

• Hazardous Substances Data: 445469-32-9(Hazardous Substances Data)

Upstream product

• 445469-30-7 (1S,2S,3R,4S,5R)-2,4-bis-(tert-butyldimethylsilanyloxy)-3-(triethylsilanyloxy)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Variable strategy toward carbasugars and relatives. 4. Viable access to (4a-carbapentofuranosyl)amines, (5a-carbahexopyranosyl)amines, and amino acids thereof

A chiral, divergent synthesis of two carbafuranosylamines, 1 and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)-oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.