[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane
• CAS No.: 225928-52-9
• Molecular Formula: C₂₅H₄₄O₄Si
• Molecular Weight: 436.707
• Mol file: 225928-52-9.mol

Synonyms:[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane

Chemical Property of [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane

There total 1 articles about [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (190712-24-4) → [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane (225928-52-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00411-6

Reference yield:

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane (225928-52-9) → (1R,2R)-2-(4-Methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propane-1,3-diol (225928-47-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / H₂ / 5 percent Pd/C / ethyl acetate

2: I₂, imidazole, Ph₃P / benzene

3: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

4: K₂CO₃ / methanol

5: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

6: TBAF / tetrahydrofuran

7: (COCl)2, Et₃N, DMSO / CH₂Cl₂

8: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

9: 79 percent / LiBH₄ / tetrahydrofuran

10: NaIO₄, buffer pH 7 / tetrahydrofuran

11: NaBH₄ / ethanol

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium borohydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(99)00411-6

Reference yield:

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane (225928-52-9) → 2,2-Dimethyl-propionic acid (2R,3R)-2-(4-methoxy-benzyloxy)-3-{(4R,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-trifluoromethanesulfonyloxy-propyl ester

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / H₂ / 5 percent Pd/C / ethyl acetate

2: I₂, imidazole, Ph₃P / benzene

3: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

4: K₂CO₃ / methanol

5: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

6: TBAF / tetrahydrofuran

7: (COCl)2, Et₃N, DMSO / CH₂Cl₂

8: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

9: 79 percent / LiBH₄ / tetrahydrofuran

10: NaIO₄, buffer pH 7 / tetrahydrofuran

11: NaBH₄ / ethanol

12: 83 percent / pyridine

13: pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium borohydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(99)00411-6

upstream raw materials:

tert-butyldimethylsilyl chloride

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Downstream raw materials:

(4R,5S)-5-[(E)-(S)-7-(4-Methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

{(4S,5S)-5-[(E)-(S)-7-(4-Methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol

tert-Butyl-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy}-dimethyl-silane

(1R,2R)-2-(4-Methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propane-1,3-diol