((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

Base Information

Chemical Name:((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol
CAS No.:863642-77-7
Molecular Formula:C₁₅H₁₉FO₃
Molecular Weight:266.312
Hs Code.:

Synonyms:((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

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Chemical Property of ((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

Chemical Property:

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Technology Process of ((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

There total 6 articles about ((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

: 863642-46-0
(3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluorotetrahydrofuran-2-yl acetate

: 762-72-1
allyl-trimethyl-silane

: 863642-77-7
((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

: 1-allyl-3,5-di-O-benzyl-2-fluoro-2-deoxyribose

: allyl 3,5-di-O-benzyl-1,2-dideoxy-2-fluoro-α-D-ribofuranoside

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 - 22 ℃; for 2h;
DOI:10.1021/ja0524043

Reference yield:

: 863642-44-8
methyl 3,5-di-O-benzyl-2-deoxy-2-fluoro-α/β-D-ribofuranoside

: 863642-77-7
((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 54 percent / aq. TFA / 5 h

2: 93 percent / pyridine; DMAP / 16 h / 22 °C

3: 50 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 - 22 °C

With pyridine; dmap; titanium tetrachloride; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ja0524043

Reference yield:

: (3S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-yl trifluoromethanesulfonate

: 863642-77-7
((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: 0.682 g / TBAF / tetrahydrofuran / 0 - 22 °C

2: 54 percent / aq. TFA / 5 h

3: 93 percent / pyridine; DMAP / 16 h / 22 °C

4: 50 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 - 22 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; titanium tetrachloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja0524043