233589-82-7

Upstream product

• 1374633-07-4 p-methoxyphenyl 2-O-benzyl-3,4-O-isopropylidene-6-O-trityl-β-d-galactopyranoside 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 503303-06-8 p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside 
• 503303-07-9 p-methoxyphenyl 3,4-O-isopropylidene-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 233589-87-2 N-{(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-2,2,2-trichloro-acetamide 
• 233589-86-1 2,2,2-Trichloro-acetimidic acid (E)-(S)-4-benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enyl ester 
• 233589-88-3 {(S)-1-[(S)-Benzyloxy-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-allyl}-carbamic acid tert-butyl ester 
• 233589-89-4 ((3aS,4S,5S,7aS)-4-Benzyloxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-carbamic acid tert-butyl ester 
• 233589-84-9 (E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester 
• 233589-97-4 (Z)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester 
• 233589-93-0 (S)-2-[(S)-Benzyloxy-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-but-3-en-1-ol 
• 233589-94-1 (R)-2-[(S)-Benzyloxy-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-methyl]-but-3-en-1-ol 
• 233589-85-0 (E)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol 
• 233589-98-5 (Z)-(S)-4-Benzyloxy-4-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol 
• 73111-80-5 (2R,3S,4S)-3,4-isopropylidenedioxy-2-benzyloxyhex-5-enal 
• 233589-83-8 (3aR,4S,6S,7R,7aS)-7-Benzyloxy-4-iodomethyl-6-(4-methoxy-phenoxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 

Relevant academic research and scientific papers

Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy- d - Manno -oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- And β-Kdo Glycosides

The stereodirecting effect of C5-ester functions on the glycosylation stereoselectivity of 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) ethyl thioglycoside donors is presented. The coupling of 5-O-arylcarbonyl or acetyl protected Kdo thioglycosides with acceptors proceeds in an α-selective and high-yielding manner, leading to formation of α-linked Kdo glycosides products. On the other hand, the glycosylation stereoselectivity of the 5-O-2-quinolinecarbonyl (Quin) or 4-nitropicoloyl substituted Kdo thioglycoside donors is switchable: (1) The glycosylation of the 5-O-Quin carrying Kdo donors with primary glycosyl acceptors shows complete β-stereoselectivity, furnishing the corresponding β-glycosides in good-to-excellent yield. (2) The stereochemical outcome of the secondary acceptors with these Kdo donors is determined mainly by the stereoelectronic nature of the acceptor. Only or predominant α anomeric products are obtained when the Kdo donors couple with the disarmed or highly crowded secondary carbohydrate acceptors, while the selectivity may switch to predominant β in the glycosylation of the 5-O-4-nitropicoloyl carrying donor with more reactive secondary alcohols. The synthetic use of the newly developed Kdo donors 1c and 7b has been demonstrated by facile preparation of a structurally unique trisaccharide motif 19 which possesses both α- and β-Kdo glycosidic bonds.

A versatile approach to the synthesis of highly functionalised carbocycles

A synthetic route towards conduramine and carbasugar derivatives based on the transformation (i.e. two-carbon Wittig olefination and ester reduction) of the Vasella rearrangement product derived from D-galactose followed by either a [3,3] Overman or a [2,3]-Wittig-Still sigmatropic rearrangement, and subsequent ring-closing metathesis, is presented.