81348-26-7

Upstream product

• 100-39-0 benzyl bromide 
• 14897-47-3 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 104530-15-6 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 
• 121686-51-9 methyl 2-O-benzyl-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 104477-38-5 (3aS,4R,6R,7R,7aS)-7-Benzyloxy-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 114244-04-1 methyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 110319-35-2 methyl 6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 

Downstream Products

• 15038-69-4 methyl 2-O-benzyl-β-D-galactopyranoside 
• 143916-27-2 methyl 2-O-benzyl-4-deoxy-α-L-threo-hex-4-enodialdo-1,5-pyranoside 
• 104477-40-9 methyl 6-O-acetyl-2-O-benzyl-β-galactopyranoside 
• 39946-31-1 methyl 2-O-benzyl-6-deoxy-3,4-O-isopropylidene-β-D-galactoside 
• 306300-04-9 methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside 
• 207346-81-4 methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-enopyranoside 
• 306300-19-6 methyl 2-O-benzyl-7,7-dibromo-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-enopyranoside 
• 740840-43-1 3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (2R)-2-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(2'-ethanoate))-3,4-O-isopropylidene-2,6,7-trideoxy-β-D-galacto-octopyranosid)uronate 
• 740841-03-6 3'',4'',6''-tri-O-benzyl-1'',2''-dideoxy-D-arabino-hex-1''-enyl (methyl (2S)-2-C-((3',4',6'-tri-O-benzyl-1',2'-dideoxy-D-arabino-hex-1'-enyl)-(2'-ethanoate))-2,3-O-isopropylidene-2,6,7-trideoxy-β-D-galacto-octopyranosid)uronate 
• 740840-39-5 3-((3aS,4R,6R,7R,7aS)-6-Methoxy-2,2-dimethyl-7-phenoxythiocarbonyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-propionic acid ethyl ester 
• 740840-37-3 (E)-3-((3aS,4R,6R,7R,7aS)-7-Benzyloxy-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-acrylic acid ethyl ester 
• 207602-77-5 methyl 2-O-benzyl-6-deoxy-6-iodo-3,4-O-isopropylidene-β-D-galactopyranoside 
• 104477-39-6 Acetic acid (3aS,4R,6R,7R,7aS)-7-benzyloxy-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis of vinyl- and alkynylcyclopentanetetraols by SmI2/Pd(0)-promoted carbohydrate ring-contraction

A variety of vinyl- or alkynyl-substituted polyhydroxylated cyclopentanes and cyclobutanes are prepared in enantiomerically pure form from appropriate carbohydrate precursors, in a direct one-step ring-contraction procedure promoted by SmI2 and catalytic Pd(0). This reaction is thought to proceed through intermediate ring-opened allyl- or allenylsamarium complexes that undergo ring-closure by intramolecular carbonyl addition. A predominant trans relationship is found between vinyl (or alkynyl) and hydroxyl groups at the two newly created stereogenic centers, with good to excellent levels of stereoselectivity being observed in the formation of homopropargyl cyclopentanol products. Under appropriate conditions, preparatively useful yields are realized of stereoisomers not directly available using alternative methodology.

A new synthesis of L-ascorbic acid from D-galactose

1,5-Anhydro-D-galactitol, easily available from D-galactose, was selectively protected in positions 2, 3 and 4 and converted into 5-O-acetyl-2,6-anhydro-3-deoxy-L-threo-hex-2-enonic acid methyl ester, which, on reaction with MCPBA in acetic acid gave 2,5-di-O-acetyl-α-L-lyxo-hex-2-ulopyranosonic acid methyl ester. Reaction of the latter with sodium methoxide produced sodium L-ascorbate in high yield. Several side-reactions and the conformations of some of the intermediates are also discussed.

SYNTHESYS OF O-α-L-FUCOPYRANOSYL-(1->3)-O-β-D-GALACTOPYRANOSYL-(1->4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE (N-ACETYL-3'-O-α-L-FUCOPYRANOSYLLACTOSAMINE)

Methyl 2-O-benzyl-β-D-galactopyranoside (6) was obtained in five, good yielding steps from methyl β-D-galactopyranoside (1).Treatment of 1 with tert-butylchlorodiphenylsilane in N,N-dimethylformamide in the presence of imidazole afforded a 6-(tert-butyldi

NEW RESULTS IN THE ISOPROPYLIDENATION OF GALACTOPYRANOSIDES. USEFUL INTERMEDIATES FOR THE SYNTHESIS OF GALACTOSE DERIVATIVES.

Reaction of several α- and β-galactopyranosides with 2,2-dimethoxypropane produced up to five types of mono-, bis-, and tris(isopropylidene)acetals, among which the 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl) derivatives can be obtained in high yield an