{1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane
• CAS No.: 362624-07-5
• Molecular Formula: C₂₂H₃₆O₄Si
• Molecular Weight: 392.611

Synonyms:{1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane

Chemical Property of {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane

There total 10 articles about {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-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) + (R)-1-[2-(2-Benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-but-3-en-2-ol (362624-06-4) → {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane (362624-07-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol (5694-95-1) → {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane (362624-07-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / NaH / tetrahydrofuran / 0 °C

2: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

3: CH₂Cl₂

4: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

5: 82 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 9 h / -20 °C

6: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

7: 95 percent / Zn; NaI / methanol / Heating

8: 97 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; iodine; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; titanium(IV) isopropylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Swern oxidation / 3: Wittig olefination / 5: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

dimethyl acetonedicarboxylate ethylene ketal (6506-31-6) → {1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane (362624-07-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / LiAlH₄ / tetrahydrofuran / Heating

2: 75 percent / NaH / tetrahydrofuran / 0 °C

3: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

4: CH₂Cl₂

5: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 82 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 9 h / -20 °C

7: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

8: 95 percent / Zn; NaI / methanol / Heating

9: 97 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; lithium aluminium tetrahydride; oxalyl dichloride; iodine; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium iodide; zinc; titanium(IV) isopropylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Swern oxidation / 4: Wittig olefination / 6: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4039(01)00841-3

upstream raw materials:

tert-butyldimethylsilyl chloride

(R)-1-[2-(2-Benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-but-3-en-2-ol

2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol

dimethyl acetonedicarboxylate ethylene ketal

Downstream raw materials:

(E)-2-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-6-{2-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxymethoxy-propyl]-[1,3]dioxolan-2-yl}-2-methyl-hex-4-en-3-one

3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

{2-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-1-methoxymethoxymethyl-ethoxy}-tert-butyl-dimethyl-silane

3-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

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