tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane
• CAS No.: 1352577-39-9
• Molecular Formula: C₃₄H₅₁IO₃Si₂
• Molecular Weight: 690.853
• Mol file: 1352577-39-9.mol

Synonyms:tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane

Chemical Property of tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane

There total 11 articles about tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane 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: 44.0%

iodoform (75-47-8) + (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde (1352577-34-4) → C34H52O4Si2 + tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane (1352577-39-9)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; at 0 - 23 ℃; for 5.08333h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

(S,Z)-5-((2S,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-methoxy-2-methyltetrahydro-2H-pyran-2-yl)-2,2,3,3,12,12-hexamethyl-11,11-diphenyl-4,10-dioxa-3,11-disilatridec-6-ene (1352577-32-2) → C34H52O4Si2 + tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane (1352577-39-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tin(IV) chloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 23 °C / Inert atmosphere

3.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3.5 h / 23 °C

4.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16.25 h / 23 - 35 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 20 h / 75 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

6.2: 1.5 h / -40 - 23 °C / Inert atmosphere

7.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.12 h / 0 - 23 °C / Inert atmosphere; Molecular sieve

9.1: chromium dichloride / tetrahydrofuran / 5.08 h / 0 - 23 °C / Inert atmosphere

With pyridine; chromium dichloride; dmap; sodium chlorite; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; tin(IV) chloride; benzotriazol-1-ol; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid (1352577-48-0) → C34H52O4Si2 + tert-butyl((2-(1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-((E)-2-iodovinyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane (1352577-39-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16.25 h / 23 - 35 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 20 h / 75 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

3.2: 1.5 h / -40 - 23 °C / Inert atmosphere

4.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.12 h / 0 - 23 °C / Inert atmosphere; Molecular sieve

6.1: chromium dichloride / tetrahydrofuran / 5.08 h / 0 - 23 °C / Inert atmosphere

With pyridine; chromium dichloride; dmap; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; benzotriazol-1-ol; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1016/j.tet.2011.09.079

upstream raw materials:

(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid

(1S,2S,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

(1S,2R,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

2-((1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-(hydroxymethyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethanol

Downstream raw materials:

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)-3-(phenylselanyl)pyrrolidin-2-one

N-benzoyl-O-tert-butyldimethylsilyl-aspergillin PZ