(3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole
• CAS No.: 1352945-24-4
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 1352945-24-4.mol

Synonyms:(3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole

Chemical Property of (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole

There total 5 articles about (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-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: 96.7%

C23H28O7S (1352945-44-8) → (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole (1352945-24-4)

Guidance literature:

C₂₃H₂₈O₇S; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 75 ℃; for 5h; Inert atmosphere;

With water; In tetrahydrofuran; ethyl acetate; at 0 ℃;

DOI:10.1016/j.tetlet.2011.10.076

Reference yield:

(2R,5S)-2-(benzyloxymethyl)-5-methyltetrahydrofuran-3,4-diol + 2,2-dimethoxy-propane (77-76-9) → (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole (1352945-24-4) + (3aS,4R,6S,6aR)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole (1392482-39-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; at 20 ℃; for 23h; Inert atmosphere;

DOI:10.1039/c2ob25069a

Reference yield:

1,3-diphenyl-2-(2,3-O-isopropylidene-β-D-ribofuranosil)-imidazolidine (85735-13-3) → (3aR,4R,6S,6aS)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole (1352945-24-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine / 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 75 °C / Inert atmosphere

4.2: 0 °C

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.10.076

upstream raw materials:

C₂₃H₂₈O₇S

benzyl bromide

1,3-diphenyl-2-(2,3-O-isopropylidene-β-D-ribofuranosil)-imidazolidine

2-(5-O-benzyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-1,3-diphenylimidazolidine

Downstream raw materials:

(2R,3S,4R,5S,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

tert-butyldimethyl(2-((E)-2-((3aR,4R,6S,6aS)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyloxy)silane

(3aR,4R,6S,6aS)-4-(3-methoxystyryl)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]dioxole

(3aS,4S,6R,6aR)-2,2,4-trimethyl-6-styryltetrahydrofuro-[3,4-d][1,3]dioxole