1255906-08-1

Basic information

• Product Name: C₁₅H₁₉NO₃
• Synonyms: C₁₅H₁₉NO₃
• CAS NO: 1255906-08-1
• Molecular Weight: 261.321
• Mol File: 1255906-08-1.mol

Chemical Properties

• CAS DataBase Reference: C₁₅H₁₉NO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₅H₁₉NO₃(1255906-08-1)
• EPA Substance Registry System: C₁₅H₁₉NO₃(1255906-08-1)

Safety Data

• Hazardous Substances Data: 1255906-08-1(Hazardous Substances Data)

Upstream product

• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 16667-96-2 O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate 
• 4613-62-1 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 4613-68-7 O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose 
• 100-46-9 benzylamine 

Downstream Products

• 1365659-13-7 (3R,5S)-5-[((phenylmethyl(benzyloxycarbonyl)amino)methyl)-2-(R/S)-methoxy-tetrahydrofuran-3-yl]methanesulfonate 
• 1365659-10-4 N-benzyl-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanamine 
• 1365659-11-5 benzyl benzyl((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)carbamate 
• 1365659-12-6 benzyl benzyl(((3R)-hydroxy-2(R/S)-methoxy-(5S)-tetrahydrofuran2-yl)methyl)carbamate 

Relevant articles and documents

Synthesis of (2S,4S)-4-hydroxyproline from D-glucose

Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.

The synthesis of (1S,8aS)-1-hydroxyindolizidine using a stereoselective Grignard addition to an N-benzyl-3-deoxy sugar imine derived from D-Glucose

A highly stereoselective approach to 1-hydroxyindolizidine is described using a Grignard reaction on N-benzyl imine derived from 3-deoxy-1,2-O- isopropylidine-α-d-xylo-pentodialdofuranose and reductive cyclization as key steps.