4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol

Base Information

• Chemical Name: 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol
• CAS No.: 362624-08-6
• Molecular Formula: C₂₂H₃₈O₆Si
• Molecular Weight: 426.626

Synonyms:4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol

Chemical Property of 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol

There total 11 articles about 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol 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: 90.0%

{1-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-allyloxy}-tert-butyl-dimethyl-silane (362624-07-5) → 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol (362624-08-6)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; 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) → 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol (362624-08-6)

Guidance literature:

Multi-step reaction with 9 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

9: 90 percent / OsO₄; NMO / acetone; H₂O / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; 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; water; N,N-dimethyl-formamide; acetone; 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) → 4-[2-(2-benzyloxy-ethyl)-[1,3]dioxolan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-butane-1,2-diol (362624-08-6)

Guidance literature:

Multi-step reaction with 10 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

10: 90 percent / OsO₄; NMO / acetone; H₂O / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 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; water; N,N-dimethyl-formamide; acetone; acetonitrile; 3: Swern oxidation / 4: Wittig olefination / 6: Sharpless asymmetric epoxidation;

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

upstream raw materials:

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

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

dimethyl acetonedicarboxylate ethylene ketal

3-oxopentanedioic acid dimethyl ester

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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