((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

Base Information

Chemical Name:((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol
CAS No.:1413282-23-1
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

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Chemical Property of ((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

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Technology Process of ((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

There total 4 articles about ((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-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:

: 1413282-16-2
(3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-3a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d]-[1,3]dioxol-4(3aH)-one

: 54655-07-1
lithium trimethylsilylacetylenide

: 1413282-17-3
((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

: 1413282-23-1
((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

Guidance literature:: (3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-3a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d]-[1,3]dioxol-4(3aH)-one; lithium trimethylsilylacetylenide; In tetrahydrofuran; at -78 - -10 ℃;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; Enzymatic reaction;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4h;
DOI:10.1021/jo302198v

Reference yield:

: 198969-39-0
5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

: 1413282-23-1
((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium carbonate / methanol / 30 h / 90 °C

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: Ag₂CO₃ impregnated on Celite / toluene / 3 h / Reflux

4.1: tetrahydrofuran / -78 - -10 °C

4.2: Enzymatic reaction

4.3: 4 h / 0 °C

With Ag₂CO₃ impregnated on Celite; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/jo302198v

Reference yield:

: 5-O-benzyl-2-C-(((tert-butyldimethylsilyl)oxy)methyl)-2,3-O-isopropylidene-D-ribofuranose

: 1413282-23-1
((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: Ag₂CO₃ impregnated on Celite / toluene / 3 h / Reflux

2.1: tetrahydrofuran / -78 - -10 °C

2.2: Enzymatic reaction

2.3: 4 h / 0 °C

With Ag₂CO₃ impregnated on Celite; In tetrahydrofuran; toluene;
DOI:10.1021/jo302198v