184155-60-0

Upstream product

• 157903-84-9 3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene 
• 374900-65-9 acetic acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 80738-62-1 2-O-acetyl-3,4,6-tri-O-benzyl-1,5-anhydro-D-arabino-hex-1-enitol 
• 106-95-6 allyl bromide 
• 184155-59-7 (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran 
• 82659-52-7 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 1419172-77-2 (3aR,5R,6S,7R,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-butyl-octahydropyrano[3,2-b]pyrrole 
• 1419172-79-4 (3aR,5R,6S,7R,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)-methyl]-1-(2-hydroxyethyl)-octahydropyrano[3,2-b]pyrrole 
• 1419172-62-5 3,7-anhydro-5,6,8-tri-O-benzyl-2-deoxy-D-manno-octos-4-ulose 
• 1610594-38-1 1-deoxy-1-C-allyl-3,4,6-tri-O-benzyl-2-C-allyl-α-D-glucopyranoside 
• 1610594-45-0 C₃₃H₃₈O₅ 
• 184155-63-3 1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene 
• 374900-66-0 3-C-(3,6-di-O-benzyl-4-deoxy-α-D-glycero-2-ulopyranosyl)propene 
• 184155-61-1 (2R,4R,5S,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-dihydro-pyran-3-one O-methyl-oxime 

Relevant academic research and scientific papers

A convenient and highly stereoselective method for synthesis of octahydropyrano[3,2-b]pyrrole derivatives

The octahydropyrano[3,2-b]pyrrole derivatives are synthesized by a double reductive amination from pyranose derivatives of nono-2,5-diuloses and octos-4-uloses and various amines. The cyclization proceeded smoothly in the presence of sodium triacetoxyborohydride to produce a series of novel fused N-heterobicyclic compounds with high stereoselectivity.

Synthesis of 2-deoxy-2-C-alkyl glycal and glycopyranosides from 2-hydroxy glycal ester

A method to convert 2-hydroxy glycal ester to the corresponding 2-deoxy-2-C-alkyl glycal in a facile manner, through key reactions including (i) C-allylation at C-1, (ii) Wittig reaction, and (iii) Cope rearrangement of a 1,5-diene derivative, is reported. The α-anomer of the 1,5-diene derivative underwent Cope rearrangement to afford 2-deoxy-2-C-glycal derivative, whereas the β-anomer was found to be unreactive. Employing this sequence, 3,4,6-tri-O-benzyl-2-O-acetyl-1,5-anhydro-d-arabino-hex-1-enitol was transformed to 3,4,6-tri-O-benzyl-2-deoxy-2-C-alkyl-1,5-anhydro-d-arabino-hex-1-enitol. 2-Deoxy-2-C-alkyl glycal derivative is a suitable glycosyl donor to prepare 2-deoxy-2-C-alkyl glycosides, mediated through haloglycosylation and a subsequent dehalogenation. A number of 2-deoxy-2-C-alkyl glycosides, with both glycosyl and nonglycosyl moieties at the reducing end, are thus prepared from the glycal.

Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: A stereospecific rearrangement initiated by base

Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4α, 4β, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a β elimination to afford α,β-unsaturated C-ulopyranosyl compounds (5α, 5β, and 12), which further rearranged in a stereocontrolled manner to multifunctionalized α,β-cyclopentenones (6 and 14) in 70-80% yield. Both C-α- and C-β-2-ulosides (5α and 5β) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5α yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5α during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used.