(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

Base Information

• Chemical Name: (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
• CAS No.: 909576-49-4
• Molecular Formula: C₂₆H₃₂O₆
• Molecular Weight: 440.536
• Mol file: 909576-49-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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:

benzyl bromide (100-39-0) + (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,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 (909576-49-4)

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 mercury dichloride; In water; at 20 ℃; for 1h;

With sodium tetrahydroborate; oxygen; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2006.06.049

Reference yield: 78.0%

(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 (909576-49-4) → (2R,3S,4R)-3-Benzyloxy-4-((2S,5S)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2,4-dihydroxy-butyraldehyde (909576-59-6)

Guidance literature:

With sulfuric acid; In water; acetic acid; at 80 ℃; for 7h;

DOI:10.1016/j.tetlet.2006.06.049

Reference yield:

(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 (909576-49-4) → ((2S,3R,5S,2'S,5'S)-3-Benzyloxy-5'-benzyloxymethyl-octahydro-[2,2']bifuranyl-5-yl)-methanol

Guidance literature:

Multi-step reaction with 7 steps

1.1: 78 percent / H₂SO₄ / acetic acid; H₂O / 7 h / 80 °C

2.1: 88 percent / tetrahydrofuran / 4 h / 20 °C

3.1: HgCl₂ / H₂O / 2 h / 20 °C

3.2: O₂; NaBH₄ / dimethylformamide / 4 h / 20 °C

4.1: 92 percent / imidazole / 5 h / 20 °C

5.1: 93 percent / NaH / tetrahydrofuran / 2 h / 0 °C

6.1: 94 percent / Bu₃SnH; AIBN / toluene / 3 h / 90 °C

7.1: 89 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); sulfuric acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; mercury dichloride; In tetrahydrofuran; water; acetic acid; toluene; 2.1: Wittig reaction;

DOI:10.1016/j.tetlet.2006.06.049

upstream raw materials:

benzyl bromide

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

Downstream raw materials:

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

(1R,2R,3S)-2-Benzyloxy-1-((2S,5S)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-pent-4-ene-1,3-diol

(2R,3R,4S,5R,2'S,5'S)-3-Benzyloxy-5'-benzyloxymethyl-5-hydroxymethyl-octahydro-[2,2']bifuranyl-4-ol

((2S,3R,5S,2'S,5'S)-3-Benzyloxy-5'-benzyloxymethyl-octahydro-[2,2']bifuranyl-5-ylmethoxy)-tert-butyl-dimethyl-silane