1273232-31-7

Basic information

• Product Name: tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate
• Synonyms: tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate
• CAS NO: 1273232-31-7
• Molecular Weight: 475.626
• Mol File: 1273232-31-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate(1273232-31-7)
• EPA Substance Registry System: tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate(1273232-31-7)

Safety Data

• Hazardous Substances Data: 1273232-31-7(Hazardous Substances Data)

Upstream product

• 1258980-78-7 (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amine 
• 1085845-83-5 tert-butyl (2E,4S,5R)-4,5-O-isopropylidene-hepta-2,6-dienoate 
• 532-20-7 D-Ribose 
• 6298-96-0 1(R)-(4-methoxyphenyl)-ethylamine 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 38838-06-1 methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 

Downstream Products

• 1273232-35-1 (1R,2S,3S,7S,7aS,1'R)-1,2-O-isopropylidene-3-(1'-hydroxy-2'-tert-butoxy-2'-oxoethyl)-7-iodooctahydropyrolizinium iodide 
• 67233-95-8 α-methyl-p-methoxybenzyl ethyl ether 

Relevant articles and documents

Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular iodoamination with concomitant N-debenzylation

The doubly diastereoselective "matched" conjugate addition of lithium (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl (4S,5R,E)-4,5-O-isopropylidene-2,7-dienoate (derived from d-ribose in 3 steps) and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine was followed by ring-closing metathesis with Grubbs I to give a hexahydroazocine scaffold. Subsequent treatment with I2 resulted in transannular iodoamination accompanied by loss of the α-methyl-p-methoxybenzyl group to give the corresponding pyrrolizidine scaffold as a single diastereoisomer upon direct crystallization from the crude reaction mixture. Further functional group manipulations enabled the preparation of (-)-7a-epi-hyacinthacine A1.