(((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane

Base Information

Chemical Name:(((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane
CAS No.:1413282-22-0
Molecular Formula:C₂₄H₃₆O₅Si
Molecular Weight:432.632
Hs Code.:

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

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

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

There total 4 articles about (((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane 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

: 1413282-12-8
(((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane

: 1413282-22-0
(((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane

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 potassium carbonate; In methanol; dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jo302198v

Reference yield:

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

: 1413282-22-0
(((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane

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 / 20 °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

: 1413282-22-0
(((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane

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 / 20 °C

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