(2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane

Base Information

• Chemical Name: (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane
• CAS No.: 887001-91-4
• Molecular Formula: C₃₁H₄₃IO₄Si
• Molecular Weight: 634.67
• Mol file: 887001-91-4.mol

Synonyms:(2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane

Chemical Property of (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane

There total 17 articles about (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane 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:

(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-al (858666-69-0) → (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane (887001-91-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

2.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

3.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

4.1: 84 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 80 °C

5.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

6.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

7.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

8.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

9.1: 71 percent / 4 Angstroem molecular sieves; (+)-diethyl L-tartrate; tert-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 4 h / -20 °C

10.1: Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 1 h / 0 °C

11.1: 10 mg / NaI; NaHCO₃ / acetone / 24 h / 50 °C

With pyridine; tert.-butylhydroperoxide; dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; diisobutylaluminum hydride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; sodium iodide; titanium(IV) isopropylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetone; toluene; 7.1: Wittig olefination;

DOI:10.1039/b600951d

Reference yield:

(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane (858666-87-2) → (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane (887001-91-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

2: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3: 99 percent / CH₂Cl₂ / 20 h / 20 °C

4: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

5: 71 percent / 4 Angstroem molecular sieves; (+)-diethyl L-tartrate; tert-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 4 h / -20 °C

6: Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 1 h / 0 °C

7: 10 mg / NaI; NaHCO₃ / acetone / 24 h / 50 °C

With pyridine; tert.-butylhydroperoxide; dmap; diisobutylaluminum hydride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; sodium iodide; titanium(IV) isopropylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; toluene; 3: Wittig olefination;

DOI:10.1039/b600951d

Reference yield:

(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-ol (887001-88-9) → (2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane (887001-91-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 99 percent / pyridinium chlorochromate; potassium carbonate / CH₂Cl₂ / 3 h / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

3.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

4.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

5.1: 84 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 80 °C

6.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

7.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

8.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

9.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

10.1: 71 percent / 4 Angstroem molecular sieves; (+)-diethyl L-tartrate; tert-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 4 h / -20 °C

11.1: Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 1 h / 0 °C

12.1: 10 mg / NaI; NaHCO₃ / acetone / 24 h / 50 °C

With pyridine; tert.-butylhydroperoxide; dmap; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; diisobutylaluminum hydride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; sodium iodide; titanium(IV) isopropylate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetone; toluene; 8.1: Wittig olefination;

DOI:10.1039/b600951d

upstream raw materials:

(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

(1'E,2S,5R,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(3'-hydroxy-1'-propenyl)-1,6-dioxaspiro[4.5]decane

(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

(2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-hydroxy-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane