((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Base Information

• Chemical Name: ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS No.: 180300-78-1
• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.326
• Mol file: 180300-78-1.mol

Synonyms:((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property of ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

There total 9 articles about ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 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:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) + acetylenemagnesium bromide (4301-14-8) → ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (180300-78-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 3h; Inert atmosphere;

Reference yield:

5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-3-C-(2-trimethylsilylethynyl)-α-D-ribofuranose (155470-62-5) → 1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-C-ethynyl-α-D-ribofuranose (180300-93-0) + ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (180300-78-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

Reference yield:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → ((3aR,5R,6R,6aR)-6-ethynyl-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (180300-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1: BuLi / tetrahydrofuran / -78 °C

2: TBAF / tetrahydrofuran / 20 °C

3: pyridine / 20 °C

With pyridine; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)01249-2

upstream raw materials:

benzoyl chloride

3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentofuranose

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

methyl 5-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose

methyl 2,3,5-tri-O-benzoyl-3-C-ethynyl-α,β-D-ribofuranose

1-O-acetyl-2,3,5-tri-O-benzoyl-3-C-ethynyl-D-ribofuranose

1-(2,3,5-tri-O-benzoyl-3-C-ethynyl-β-D-ribofuranosyl)uracil