(Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol

Base Information

• Chemical Name: (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol
• CAS No.: 139195-33-8
• Molecular Formula: C₇₈H₈₄O₁₀Si
• Molecular Weight: 1209.6
• Mol file: 139195-33-8.mol

Synonyms:

Chemical Property of (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol

There total 26 articles about (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-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: 67.0%

(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((Z)-2-iodo-vinyl)-tetrahydro-pyran (110316-55-7) + (2S,3R,4S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentanal (105265-83-6,108713-94-6,108713-98-0) → (Z)-(3R,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol (139195-33-8,139242-04-9) + (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol (139195-33-8,139242-04-9)

Guidance literature:

With chromium dichloride; nickel dichloride; In dimethyl sulfoxide; for 168h; Ambient temperature;

DOI:10.1021/jo00022a039

Reference yield: 67.0%

(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((Z)-2-iodo-vinyl)-tetrahydro-pyran (110316-55-7) + (2S,3R,4S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentanal (105265-83-6,108713-94-6,108713-98-0) → (Z)-(3R,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol (139195-33-8,139242-04-9) + (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol (139195-33-8,139242-04-9)

Guidance literature:

With chromium dichloride; nickel dichloride; In dimethyl sulfoxide; for 168h; Ambient temperature;

DOI:10.1021/jo00022a039

Reference yield:

L-xylose diethyl dithioacetal (23259-79-2) → (Z)-(3R,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol (139195-33-8,139242-04-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / pyridine / 24 h / Ambient temperature

2: 1.) NaH / 1.) DMF, THF, room temperature, 1 h, 2.) room temperature, 24 h

3: 78 percent / 6 N HCl / tetrahydrofuran / 36 h / Ambient temperature

4: 97 percent / imidazole / dimethylformamide / Ambient temperature

5: 84 percent / N-bromosuccinimide, collidine, AgNO₃ / acetone; H₂O / 0.25 h / 0 °C

6: 67 percent / 0.11percent NiCl₂/CrCl₂ / dimethylsulfoxide / 168 h / Ambient temperature

With pyridine; 1H-imidazole; chromium dichloride; 2,3,5-trimethyl-pyridine; hydrogenchloride; N-Bromosuccinimide; sodium hydride; silver nitrate; nickel dichloride; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00022a039

upstream raw materials:

(2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((Z)-2-iodo-vinyl)-tetrahydro-pyran

(2S,3R,4S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentanal

L-xylose diethyl dithioacetal

benzyl bromide

Downstream raw materials:

(3R,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-heptan-3-ol

C₇₈H₈₄⁽²⁾H₂O₁₀Si