190188-69-3

Upstream product

• 107108-67-8 tert-butyl 2,3-deoxy-α-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 2873-29-2 D-glucal triacetate 
• 107108-66-7 Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-tert-butoxy-tetrahydro-pyran-3-yl ester 
• 69247-20-7 tert-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 

Downstream Products

• 167901-80-6 tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-erythro-non-8-enopyranoside 
• 190188-71-7 (S)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol 
• 190188-70-6 (R)-1-((2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-but-3-en-2-ol 
• 190188-72-8 (2R,3S,6R)-3-Benzyloxy-2-((R)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran 
• 190188-73-9 (2R,3S,6R)-3-Benzyloxy-2-((S)-2-benzyloxy-but-3-enyl)-6-tert-butoxy-tetrahydro-pyran 
• 321126-23-2 t-butyl 4-O-benzyl-6-O-tosyl-2,3-dideoxy-α-D-galacto-pyranoside 
• 321126-30-1 t-butyl 6-O-tosyl-2,3-dideoxy-α-D-galacto-pyranoside 
• 180186-85-0 C₃₆H₄₉F₃O₆ 
• 180067-18-9 C₃₆H₄₉F₃O₆ 
• 180067-20-3 (R)-4-Benzyloxy-4-((2R,5S)-5-{(R)-3-[(2R,3S,6S)-3-benzyloxy-6-(2,2,2-trifluoro-ethoxy)-tetrahydro-pyran-2-yl]-1-iodo-propyl}-tetrahydro-furan-2-yl)-butyraldehyde 
• 321126-25-4 (2R,3S,6S)-3-Benzyloxy-2-{(R)-3-[(2S,5R)-5-((R)-1-benzyloxy-pent-4-enyl)-tetrahydro-furan-2-yl]-3-iodo-propyl}-6-(2,2,2-trifluoro-ethoxy)-tetrahydro-pyran 
• 180067-21-4 (2S,5R,2'S,5'R)-5'-((R)-1-Benzyloxy-pent-4-enyl)-5-((S)-1-benzyloxy-pent-4-enyl)-octahydro-[2,2']bifuranyl 
• 321126-15-2 C₃₆H₄₉F₃O₇ 
• 321126-18-5 3-((2R,3R,6R)-3-Benzyloxy-6-tert-butoxy-tetrahydro-pyran-2-yl)-propionaldehyde 

Relevant academic research and scientific papers

A modular synthesis of the bis-tetrahydrofuran core of rolliniastatin from pyranoside precursors

The iodoetherification of C6 allyllated 2,3-dideoxypyranosides has been shown to give cis-2,5-disubstituted tetrahydrofurans in high stereoselectivity. This result is applied to a modular synthesis of the bis-THF core of the acetogenin, rolliniastatin. (C) 2000 Elsevier Science Ltd.

C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-,1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyl-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs. the non-pyranoside substrates, but the selectivity in both cases was low.