(E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol

Base Information

• Chemical Name: (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol
• CAS No.: 101906-31-4
• Molecular Formula: C₃₂H₅₄O₄Si
• Molecular Weight: 530.864
• Mol file: 101906-31-4.mol

Synonyms:

Chemical Property of (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol

There total 19 articles about (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-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:

(2S,4R,9R)-(6E)-10-benzyloxy-1,2-epoxy-7,9-dimethyldec-6-ene-4-ol (114092-17-0) → (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol (101906-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NEt₃ / dimethylformamide

With triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/c39850001388

Reference yield:

(4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane (101906-28-9) → (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol (101906-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / H⁽¹⁺⁾ / methanol

2: 95 percent / pyridine

3: 80 percent / K₂CO₃ / methanol

4: 93 percent / NEt₃ / dimethylformamide

With pyridine; hydrogen cation; potassium carbonate; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/c39850001388

Reference yield:

(S)-(+)-3-benzyloxy-2-methylpropyl bromide (63930-50-7) → (E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol (101906-31-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 51 percent / ethylenediamine / dimethylsulfoxide / 1.) 8 deg C; 2.) 20 min, r.t.

3: 83 percent / Amberlite 120 acidic exchange resin / methanol / 72 h / Ambient temperature

4: 78 percent / pyridine / 10 h / 0 °C

5: 80 percent / K₂CO₃ / methanol / 0.42 h / Ambient temperature

6: 87 percent / 4-(N,N-dimethylamino)pyridine, NEt₃ / dimethylformamide / 5 h / Ambient temperature

With dmap; Amberlite 120 acidic exchange resin; potassium carbonate; ethylenediamine; triethylamine; In pyridine; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1039/P19870002189

upstream raw materials:

(2S,4R,9R)-(6E)-1,2-epoxy-10-benzyloxy-7,9-dimethyl-4-(dimethyl-t-butylsilyloxy)dec-6-ene

(2R,3S)-2,3-dimethyl-3,44-dihydro-2H-pyran

(2S,4R,9R)-(6E)-10-benzyloxy-1,2-epoxy-7,9-dimethyldec-6-ene-4-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,4S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane

(2R,4R,6S,8R,9S)-2-<(5R)-(2E)-6-benzyloxy-3,5-dimethyl-hex-2-en-1-yl>-8,9-dimethyl-4-(dimethyl-t-butylsilyloxy)-1,7-dioxaspiro<5.5>undecane