<3aS-<3aα,4α,7aα,7α(3Z,2R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate

Base Information

• Chemical Name: <3aS-<3aα,4α,7aα,7α(3Z,2R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate
• CAS No.: 107148-31-2
• Molecular Formula: C₄₀H₅₂O₇Si
• Molecular Weight: 672.934

Synonyms:<3aS-<3aα,4α,7aα,7α(3Z,2R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate

Chemical Property of <3aS-<3aα,4α,7aα,7α(3Z,2R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate

Chemical Property:

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Technology Process of <3aS-<3aα,4α,7aα,7α(3Z,2R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate

There total 13 articles about <3aS-<3aα,4α,7aα,7α(3Z,2R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate 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: 74.0%

Benzyloxy-acetic acid (R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ylmethyl}-but-2-ynyl ester (115140-93-7) → <3aS-<3aα,4α,7aα,7α(3Z,2R*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate (107148-31-2)

Guidance literature:

With hydrogen; palladium on barium sulfate; In pyridine; for 1h; Ambient temperature;

DOI:10.1021/jo00253a021

Reference yield:

(2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol → <3aS-<3aα,4α,7aα,7α(3Z,2R*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate (107148-31-2)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

4: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

5: 1.) n-BuLi, BF₃ / 1.) THF, hexane, ether, -78 deg C, 20 min, 2.) 30 min

6: 93 percent / (+)-alpine borane / tetrahydrofuran / 24 h / Ambient temperature

7: 85 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 12 h / Ambient temperature

8: 74 percent / H₂ / 5percent Pd-BaSO₄ / pyridine / 1 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; n-butyllithium; (-)-(S)-alpine-borane; boron trifluoride; hydrogen; toluene-4-sulfonic acid; copper(II) sulfate; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; palladium on barium sulfate; In tetrahydrofuran; pyridine; dichloromethane; water; acetone; xylene;

DOI:10.1021/jo00253a021

Reference yield:

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide (115118-80-4) → <3aS-<3aα,4α,7aα,7α(3Z,2R*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-8-ethanol (phenylmethoxy)acetate (107148-31-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

2: 1.) n-BuLi, BF₃ / 1.) THF, hexane, ether, -78 deg C, 20 min, 2.) 30 min

3: 93 percent / (+)-alpine borane / tetrahydrofuran / 24 h / Ambient temperature

4: 85 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 12 h / Ambient temperature

5: 74 percent / H₂ / 5percent Pd-BaSO₄ / pyridine / 1 h / Ambient temperature

With dmap; n-butyllithium; (-)-(S)-alpine-borane; boron trifluoride; hydrogen; toluene-4-sulfonic acid; copper(II) sulfate; dicyclohexyl-carbodiimide; palladium on barium sulfate; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo00253a021

upstream raw materials:

Benzyloxy-acetic acid (R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ylmethyl}-but-2-ynyl ester

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide

3,5-hexadienoyl chloride

Downstream raw materials:

<3aS-<3aα,4α,7aα,7α(3E,2R^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-3-methyl-2-(phenylmethoxy)-4-hexanoic acid methyl ester

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