1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one

Base Information

• Chemical Name: 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one
• CAS No.: 410077-26-8
• Molecular Formula: C₂₈H₄₆O₆Si
• Molecular Weight: 506.755

Synonyms:1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one

Chemical Property of 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one

There total 8 articles about 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one 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%

t-butyldimethylsiyl triflate (69739-34-0) + 1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one (410077-62-2) → 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one (410077-26-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.003

Reference yield:

(R)-1-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-methylene-hexan-2-ol (410077-58-6) → 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one (410077-26-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 92 percent / imidazole / tetrahydrofuran / 16 h / 45 °C

2.1: 83 percent / TFA; H₂O / CH₂Cl₂ / 1 h

3.1: tosyl imidazole; sodium hydride / tetrahydrofuran / 0 - 20 °C

4.1: t-BuLi / diethyl ether / 1 h / -45 °C

4.2: diethyl ether / -78 - -25 °C

4.3: 69 percent / HMPA / diethyl ether / 2.5 h / 20 °C

5.1: 99 percent / NaH; 15-crown-5 / tetrahydrofuran / 16 h

6.1: 94 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H₂O; tetrahydrofuran / 2 h / 20 °C

7.1: 84 percent / ammonium cerium nitrate / acetonitrile; H₂O / 0.05 h / 0 °C

8.1: NMO; osmium tetraoxide / acetone; H₂O / 16 h

8.2: HClO₄; Ca(ClO₄)2*4H₂O / CH₂Cl₂; acetonitrile; H₂O / 0.83 h

8.3: 66 percent / NaIO₄ / methanol; H₂O / 0.33 h

9.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; 15-crown-5; water; tert.-butyl lithium; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; p-toluenesulfonyl imidazole; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/ol017273z

Reference yield:

tert-Butyl-dimethyl-((R)-3-methylene-1-(S)-1-oxiranylmethyl-pentyloxy)-silane (410077-32-6) → 1-[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-butan-2-one (410077-26-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / diethyl ether / 1 h / -45 °C

1.2: diethyl ether / -78 - -25 °C

1.3: 69 percent / HMPA / diethyl ether / 2.5 h / 20 °C

2.1: 99 percent / NaH; 15-crown-5 / tetrahydrofuran / 16 h

3.1: 94 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H₂O; tetrahydrofuran / 2 h / 20 °C

4.1: 84 percent / ammonium cerium nitrate / acetonitrile; H₂O / 0.05 h / 0 °C

5.1: NMO; osmium tetraoxide / acetone; H₂O / 16 h

5.2: HClO₄; Ca(ClO₄)2*4H₂O / CH₂Cl₂; acetonitrile; H₂O / 0.83 h

5.3: 66 percent / NaIO₄ / methanol; H₂O / 0.33 h

6.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; 15-crown-5; tert.-butyl lithium; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/ol017273z

upstream raw materials:

t-butyldimethylsiyl triflate

1-((2S,4S,6S,8R,10S)-8-Benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl)-butan-2-one

(R)-1-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-methylene-hexan-2-ol

tert-Butyl-dimethyl-((R)-3-methylene-1-(S)-1-oxiranylmethyl-pentyloxy)-silane

Downstream raw materials:

C₆₅H₁₁₂O₁₅Si₃

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