(R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

Base Information

Chemical Name:(R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one
CAS No.:208174-50-9
Molecular Formula:C₂₃H₃₆O₇Si
Molecular Weight:452.62
Hs Code.:

Synonyms:(R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

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Chemical Property of (R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

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Technology Process of (R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

There total 8 articles about (R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one 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:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 208174-50-9
(R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

2: (COCl)2, DMSO

3: LDA / tetrahydrofuran / -78 - 20 °C

4: H₂O, InCl₃ / Ambient temperature; various Lewis acids, times

With dmap; indium(III) chloride; oxalyl dichloride; water; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/a800486b

Reference yield:

: 100-39-0
benzyl bromide

: 208174-50-9
(R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaH, Bu₄NI / tetrahydrofuran / 48 h / Ambient temperature

2: H₂₀, HCl / methanol / 72 h / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

4: (COCl)2, DMSO

5: LDA / tetrahydrofuran / -78 - 20 °C

6: H₂O, InCl₃ / Ambient temperature; various Lewis acids, times

With hydrogenchloride; dmap; indium(III) chloride; oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/a800486b

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 208174-50-9
(R)-1-((3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: H₂₀, HCl / methanol / 72 h / Ambient temperature

2: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

3: (COCl)2, DMSO

4: LDA / tetrahydrofuran / -78 - 20 °C

5: H₂O, InCl₃ / Ambient temperature; various Lewis acids, times

With hydrogenchloride; dmap; indium(III) chloride; oxalyl dichloride; water; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/a800486b