135192-43-7

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 213681-58-4 O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate 
• 211947-53-4 (2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl benzoate 
• 148926-02-7 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 250273-77-9 1,2-Di-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 216668-54-1 2,2-Dimethyl-3-oxo-butyric acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yl ester 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 

Downstream Products

• 138925-06-1 2',6'-dimethoxyphenyl O-(2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 135192-48-2 2,6-dimethoxyphenyl 3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucopyranoside 
• 213681-60-8 {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester 
• 216668-74-5 Acetic acid (2S,3S,4S,6S)-4-benzyloxycarbonylamino-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-3-yl ester 
• 135192-52-8 2,6-dimethoxyphenyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 138925-08-3 2',6'-dimethoxyphenyl O-(2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 283154-38-1 {(2S,3S,4S,6S)-6-[(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-3-hydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester 
• 216668-80-3 (2R,3S,4S,5R,6S)-5-((2S,4S,5S,6S)-4-Amino-5-hydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-6-(2,6-dimethoxy-phenoxy)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 138925-13-0 2',6'-dimethoxyphenyl O-(3-benzamido-4-O-benzoyl-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-(1-2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 138925-15-2 2',6'-dimethoxyphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Total synthesis of vancomycin - Part 4: Attachment of the sugar moieties and completion of the synthesis

The total synthesis of vancomycin (1, Figure 1) is described. The successful plan for this synthesis involves sequential and stereoselective coupling of vancomycin aglycon acceptor 6 and glycosyl donors, trichloroacetimidate 50 and glycosyl fluoride 27 (Scheme 8). Acceptor 6 was synthesized from vancomycin aglycon (2) (Scheme 1), which was derived both by total synthesis and by semisynthesis from vancomycin itself (1) (Scheme 2). The vancosamine derivative 27 was obtained by total synthesis (Scheme 3) while the glycosyl derivative 50 was prepared from glucal (46) (Scheme 6). A number of glycosidation model studies, carried out in order to establish the final route to vancomycin (1), are also described and so are a number of failed attempts to secure the target molecule (1).

Expeditious routes to evernitrose and vancosamine derivatives and synthesis of a model vancomycin aryl glycoside

Only seven steps are required to synthesize the activated derivatives 2 and 3 of evernitrose and vancosamine from the common intermediate 1 derived from L-lactic acid. The expeditious route to 3 was followed by its efficient incorporation into a vancomyci

Stereospecific synthesis of aryl β-glucosides: An application to the synthesis of a prototype corresponding to the aryloxy carbohydrate domain of vancomycin

The reaction of 3,4,6-tri-O-benzyl-D-glucal (2) with 3,3-dimethyldioxirane gives rise to the 2α,3α-oxirane with high stereoselection. Reaction of this compound with various phenols under alkaline conditions affords aryl 2α-hydroxy-β-glycosides (3a-d). Oxi