(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate

Base Information

• Chemical Name: (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate
• CAS No.: 871094-95-0
• Molecular Formula: C₃₅H₄₁F₃O₅SSi
• Molecular Weight: 658.854

Synonyms:(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate

Chemical Property of (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate

There total 5 articles about (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate 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:

(3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydropentalen-2(1H)-one (871095-04-4) → (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate (871094-95-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 5 h / -108 °C

2.2: tetrahydrofuran; toluene / -108 - 20 °C

With dmap; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol0515762

Reference yield:

methyl (3a'S,4'R,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carboxylate (127708-13-8) → (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate (871094-95-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / i-Bu₂AlH / CH₂Cl₂ / 6 h / -78 °C

2.1: 92 percent / p-toluenesulfonic acid; acetone / 3 h

3.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

4.1: KHMDS / tetrahydrofuran; toluene / 5 h / -108 °C

4.2: tetrahydrofuran; toluene / -108 - 20 °C

With dmap; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; acetone; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol0515762

Reference yield:

[(3a'S,4'S,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalen]-4'-yl]methanol (116896-28-7) → (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate (871094-95-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / p-toluenesulfonic acid; acetone / 3 h

2.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 5 h / -108 °C

3.2: tetrahydrofuran; toluene / -108 - 20 °C

With dmap; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; acetone; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol0515762

upstream raw materials:

(3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydropentalen-2(1H)-one

methyl (3a'S,4'R,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carboxylate

[(3a'S,4'S,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalen]-4'-yl]methanol

(1S,2R,3R,5R)-7,7-(2,2-Dimethyltrimethylenedioxy)-3-hydroxybicyclo<3.3.0>octan-2-carbonsaeure-methylester

Downstream raw materials:

tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

(1R,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalene-1-carbaldehyde

5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanal

((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol

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