(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 97694-39-8
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.434
• Mol file: 97694-39-8.mol

Synonyms:(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property of (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 3 articles about (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[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: 84.0%

benzyl bromide (100-39-0) + (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (35810-59-4) → (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (97694-39-8)

Guidance literature:

(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 50 ℃; for 1h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol2029838

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (97694-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: 0.75 h / -78 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 50 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ol2029838

Reference yield:

3-C-Ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (35810-59-4,99407-49-5) + benzyl chloride (100-44-7) → (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (97694-39-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) DMSO, 1.5 h, 45 deg C, 2) 1.5 h, 55 deg C;

upstream raw materials:

3-C-Ethynyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

benzyl chloride

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

benzyl bromide

Downstream raw materials:

3-O-benzyl-3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-ethynyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol