(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol
• CAS No.: 898552-17-5
• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.537
• Mol file: 898552-17-5.mol

Synonyms:(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

Chemical Property of (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

There total 10 articles about (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-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: 88.0%

(E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-penta-2,4-dien-1-ol (898552-15-3) → (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol (898552-17-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h;

DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol (898552-08-4) → (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol (898552-17-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 1.5 h

2: CSA / methanol / 2 h

3: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

4: MeLi / tetrahydrofuran / 3 h / -78 - -10 °C

5: 88 percent / TBAF / tetrahydrofuran / 0.5 h

With 2,6-dimethylpyridine; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methyllithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation;

DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (898552-07-3) → (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol (898552-17-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / p-TsOH*H₂O / tetrahydrofuran; methanol; H₂O / 18 h

2: 2,6-lutidine / CH₂Cl₂ / 1.5 h

3: CSA / methanol / 2 h

4: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

5: MeLi / tetrahydrofuran / 3 h / -78 - -10 °C

6: 88 percent / TBAF / tetrahydrofuran / 0.5 h

With 2,6-dimethylpyridine; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; methyllithium; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 4: Swern oxidation;

DOI:10.1016/j.tetlet.2006.04.018

upstream raw materials:

(E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-penta-2,4-dien-1-ol

(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-carbaldehyde

Downstream raw materials:

(2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol

(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

((2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetaldehyde