(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

Base Information

• Chemical Name: (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol
• CAS No.: 209849-12-7
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• Mol file: 209849-12-7.mol

Synonyms:(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

Chemical Property of (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

There total 2 articles about (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol 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: 95.0%

3-chloroprop-1-ene (107-05-1) + 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose (37776-17-3) → (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol (209849-12-7)

Guidance literature:

3-chloroprop-1-ene; With iodine; magnesium; In tetrahydrofuran; at 0 ℃;

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose; In tetrahydrofuran; at -10 ℃;

DOI:10.1002/ejoc.200800649

Reference yield:

3-bromo-1-butene (22037-73-6) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 1(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol (209849-11-6) + (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol (209849-12-7)

Guidance literature:

With magnesium; Yield given. Multistep reaction. Yields of byproduct given; 1.) Et₂O, reflux, 1 h, 2.) Et₂O, 1 h;

DOI:10.1055/s-1999-3392

Reference yield: 97.0%

benzyl chloride (100-44-7) + (1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol (209849-12-7) → (3aR,6S,6aR)-6-(benzyloxy)-5-((S)-1-(benzyloxy)pent-4-enyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (1093615-93-0)

Guidance literature:

(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol; With sodium hydride; In parrafin oil; N,N-dimethyl-formamide; at 20 ℃;

benzyl chloride; In parrafin oil; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/ejoc.200800649

upstream raw materials:

3-bromo-1-butene

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

3-chloroprop-1-ene

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose

[(2R,5S)-5-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-yl]-methanol

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

(2R,3S,4R)-3-Benzyloxy-4-((2S,5S)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2,4-dihydroxy-butyraldehyde