(3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:169392-04-5
Molecular Formula:C₁₆H₂₂O₄
Molecular Weight:278.348
Hs Code.:

Synonyms:(3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

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Technology Process of (3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 2 articles about (3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 82.0%

: 58475-17-5
(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

: 100-39-0
benzyl bromide

: 169392-04-5
(3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; Ambient temperature;
DOI:10.1246/cl.1995.881

Reference yield:

: 4613-62-1
3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

: 169392-04-5
(3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: 80percent AcOH

2: Py

3: 90 percent / LiAlH₄ / tetrahydrofuran

4: 82 percent / NaH, Bu₄NI / tetrahydrofuran / Ambient temperature

With pyridine; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran;
DOI:10.1246/cl.1995.881

Reference yield:

: 169392-04-5
(3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(E)-(1R,3R)-3-benzyloxy-1-(1-hydroxy-1-methyl-ethyl)-4-methyl-6-(2-oxo-2H-chromen-7-yloxy)-hex-4-enyloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 2 M aq. HCl

2: tetrahydrofuran / Ambient temperature

3: 94 percent / TsOH / CH₂Cl₂ / 0 °C

4: 98 percent / MeI, NaHCO₃ / H₂O; tetrahydrofuran

5: 78 percent / tetrahydrofuran / -78 °C

6: 94 percent / Swern reagent

7: 99 percent / tetrahydrofuran / -78 °C

8: TsOH / Ambient temperature

9: imidazole / dimethylformamide / 0 °C

10: 83 percent / H₂, NaHCO₃ / Pd/C / ethanol / Ambient temperature

11: Swern reagent

12: BuLi / tetrahydrofuran

13: DIBAL-H / toluene

14: 98 percent / CBr₄, Ph₃P / CH₂Cl₂

15: 49 percent / NaH / dimethylformamide

16: 93 percent / Bu₄NF, AcOH / tetrahydrofuran / Ambient temperature

17: 99 percent / Ph₃P, DEAD / tetrahydrofuran / Ambient temperature

18: 85 percent / 2 M aq. HCl / tetrahydrofuran

19: 36 percent / BF₃*Et₂O

With 1H-imidazole; hydrogenchloride; n-butyllithium; swern reagent; carbon tetrabromide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; diethylazodicarboxylate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1246/cl.1995.881