674769-31-4

Upstream product

• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α,β-D-arabino-hexopyranoside 
• 674769-28-9 (2S,4aR,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 2873-29-2 D-glucal triacetate 
• 160400-66-8 methyl 2-deoxy-D-arabinopyranoside 
• 126873-07-2 methyl 3,4,6-tri-O-acetyl-2-deoxy-α/β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 674769-29-0 (2S,4aR,8R,8aS)-6,8-Dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 21090-92-6 (2R,4aR,8R,8aS)-6,8-Dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 

Downstream Products

• 135708-74-6 (1S,5R,6R)-6-Benzyloxy-5-methoxy-cyclohex-2-enol 
• 135708-73-5 (5R,6S)-6-Benzyloxy-5-methoxy-cyclohex-2-enone 
• 902151-30-8 (2S,3R)-2-Benzyloxy-5-hydroxy-3-methoxy-cyclohexanone 
• 135708-84-8 (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester 
• 135708-85-9 C₄₉H₈₄O₇Si₃ 
• 135708-69-9 (3S,4R)-3-Benzyloxy-4,6-dimethoxy-2-methylene-tetrahydro-pyran 
• 674769-41-6 Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester 
• 674769-36-9 Benzoic acid (2S,3S,4R,6R)-6-((2R,3R)-3-benzyloxy-2-hydroxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester 
• 674769-37-0 Benzoic acid (2S,3S,4R,6R)-6-((2S,3S)-3-benzyloxy-2-hydroxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester 
• 674769-43-8 Benzoic acid (2S,3S,4R,6S)-6-((2R,3R)-3-benzyloxy-2-methoxy-5,5,6-trimethyl-4-oxo-hept-6-enyl)-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester 
• 674769-38-1 Benzoic acid (1R,2R,4S,6R,7R)-7-benzyloxy-4-hydroxy-2,6-dimethoxy-9,9,10-trimethyl-8-oxo-1-vinyl-undec-10-enyl ester 
• 674769-33-6 Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-methoxy-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl ester 
• 674769-32-5 Benzoic acid (2S,3S,4R,6R)-6-allyl-2-bromomethyl-4-methoxy-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Synthesis of the C(1)-C(12) segment of peloruside A by an α-benzyloxymethyl ketone aldol strategy

The C(1)-C(12) segment of 16-membered antitumor macrolide peloruside A has been prepared by a BF3·OEt2-catalyzed Mukaiyama aldol reaction between a glucose-derived C(1)-C(7) aldehyde and a C(8)-C(12) α-benzyloxymethyl ketone. Exclusive 2,3-anti and moderate 3,5-anti/syn facial selectivity (3.5:1) was observed in the aldol reaction. The key C(1)-C(7) aldehyde contains the required stereochemistry at carbons two, three, and five, and has been efficiently prepared on multigram scales from commercial triacetyl D-glucal.

Synthetic Studies toward Rapamycin: A Solution to a Problem in Chirality Merger through Use of the Ireland Reaction

A program directed toward a total synthesis of rapamycin is described.This paper reports the synthesis of enoate 36, a fragment that would correspond to carbons 28-49 of rapamycin.The two building blocks required to reach 36 were allylic alcohol 5 and aci