58886-40-1

Basic information

• Product Name: benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside
• Synonyms: benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside
• CAS NO: 58886-40-1
• Molecular Weight: 443.497
• Mol File: 58886-40-1.mol

Chemical Properties

• CAS DataBase Reference: benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside(58886-40-1)
• EPA Substance Registry System: benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside(58886-40-1)

Safety Data

• Hazardous Substances Data: 58886-40-1(Hazardous Substances Data)

Upstream product

• 42890-17-5 benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucofuranoside 
• 58886-34-3 2,2-dibenzyloxypropane 

Downstream Products

• 74072-31-4 benzyl 2-(benzyloxycarbonyl)amino-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 74072-31-4 benzyl 2-(benzyloxycarbonylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 42890-17-5 benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucofuranoside 
• 81086-76-2 benzyl 2-deoxy-5,6-O-isopropylidene-2-methylamino-β-D-glucofuranoside 
• 81086-78-4 benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 81086-77-3 benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 81086-80-8 benzyl 2-(N-acetyl-N-methylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 81086-79-5 benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 
• 81086-82-0 benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 
• 81100-13-2 benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 
• 78674-74-5 benzyl 2-(N-benzyloxycarbonylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 
• 81086-81-9 benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 
• 81086-75-1 benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 
• 81100-12-1 benzyl 2-(N-benzyloxycarbonyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside 

Relevant articles and documents

Synthesis of prumycin and related compounds

Prumycin (1) and related compounds have been synthesized from benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-d-glucofuranoside (4). Benzoylation of 4, followed by deisopropylidenation, gave benzyl 3-O-benzoyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-d-glucofuranoside (6), which was converted, via oxidative cleavage at C-5-C-6 and subsequent reduction, into the related benzyl β-d-xylofuranoside derivative (7). Benzylation of 3-O-benzoyl-2-(benzyloxycarbonyl)-amino-2-deoxy-d-xylopyranose (8), derived from 7 by hydrolysis, afforded the corresponding derivatives (9, 11) of β- and α-d-xylopyranoside, and compound 7 as a minor product. Treatment of benzyl 3-O-benzoyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-mesyl-β-d-xylopyranoside 10, formed by mesylation of 9, with sodium azide in N,N-dimethylformamide gave benzyl 4-azido-3-O-benzoyl-2-(benzyloxy-carbonyl)amino-2,4-dideoxy-α-l-arabinopyranoside (13), which was debenzoylated to compound 14. Selective reduction of the azide group in 14, and condensation of the 4-amine with N-[N-(benzyloxycarbonyl)-d-alaninoyloxy]succinimide, gave the corresponding derivative (15) of 1. Reductive removal of the protecting groups of 15 afforded 1. Prumycin analogs were also synthesized from compound 14. Evidence in support of the structures assigned to the new derivatives is presented.