(E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester

Base Information

• Chemical Name: (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester
• CAS No.: 912281-27-7
• Molecular Formula: C₄₂H₆₂O₉Si
• Molecular Weight: 739.034

Synonyms:(E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester

Chemical Property of (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester

There total 22 articles about (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester 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:

tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (912281-33-5) → (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester (912281-27-7)

Guidance literature:

Multi-step reaction with 20 steps

1.1: thexylborane / tetrahydrofuran / 0 °C

1.2: 89 percent / aq. NaOH; H₂O₂

2.1: 99 percent / imidazole / dimethylformamide / 0 °C

3.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

4.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

5.1: TMSI; HMDS / CH₂Cl₂ / 0 °C

5.2: 92 percent / K₂CO₃ / methanol / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: n-BuLi / tetrahydrofuran / -78 °C

8.1: iPr₂NEt / CH₂Cl₂ / Heating

9.1: DDQ; NaHCO₃ / CH₂Cl₂ / 20 °C

10.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

11.1: 82 percent / MeI; NaHCO₃ / CH₂Cl₂ / Heating

12.1: 79 percent / SmI₂ / methanol; tetrahydrofuran / -78 °C

13.1: LiAlH₄ / diethyl ether / 0 °C

14.1: NaH / tetrahydrofuran / Heating

15.1: 90 percent / CSA / methanol / 0 °C

16.1: 100 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

17.1: 97 percent / dimethylformamide / 50 °C

18.1: 81 percent / DIBAL-H / CH₂Cl₂ / -78 °C

19.1: Et₃N / CH₂Cl₂ / 20 °C

20.1: CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; oxalyl dichloride; trimethylsilyl iodide; thexylborane; camphor-10-sulfonic acid; hydrogen; iodine; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 6.1: Swern oxidation / 20.1: Wittig olefination;

DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol (912281-34-6) → (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester (912281-27-7)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 99 percent / imidazole / dimethylformamide / 0 °C

2.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

3.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

4.1: TMSI; HMDS / CH₂Cl₂ / 0 °C

4.2: 92 percent / K₂CO₃ / methanol / 20 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

7.1: iPr₂NEt / CH₂Cl₂ / Heating

8.1: DDQ; NaHCO₃ / CH₂Cl₂ / 20 °C

9.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

10.1: 82 percent / MeI; NaHCO₃ / CH₂Cl₂ / Heating

11.1: 79 percent / SmI₂ / methanol; tetrahydrofuran / -78 °C

12.1: LiAlH₄ / diethyl ether / 0 °C

13.1: NaH / tetrahydrofuran / Heating

14.1: 90 percent / CSA / methanol / 0 °C

15.1: 100 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

16.1: 97 percent / dimethylformamide / 50 °C

17.1: 81 percent / DIBAL-H / CH₂Cl₂ / -78 °C

18.1: Et₃N / CH₂Cl₂ / 20 °C

19.1: CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; oxalyl dichloride; trimethylsilyl iodide; camphor-10-sulfonic acid; hydrogen; iodine; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 5.1: Swern oxidation / 19.1: Wittig olefination;

DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (912281-13-1) → (E)-4-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-2-methyl-penta-2,4-dienoic acid ethyl ester (912281-27-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

2.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

3.1: TMSI; HMDS / CH₂Cl₂ / 0 °C

3.2: 92 percent / K₂CO₃ / methanol / 20 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: n-BuLi / tetrahydrofuran / -78 °C

6.1: iPr₂NEt / CH₂Cl₂ / Heating

7.1: DDQ; NaHCO₃ / CH₂Cl₂ / 20 °C

8.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

9.1: 82 percent / MeI; NaHCO₃ / CH₂Cl₂ / Heating

10.1: 79 percent / SmI₂ / methanol; tetrahydrofuran / -78 °C

11.1: LiAlH₄ / diethyl ether / 0 °C

12.1: NaH / tetrahydrofuran / Heating

13.1: 90 percent / CSA / methanol / 0 °C

14.1: 100 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

15.1: 97 percent / dimethylformamide / 50 °C

16.1: 81 percent / DIBAL-H / CH₂Cl₂ / -78 °C

17.1: Et₃N / CH₂Cl₂ / 20 °C

18.1: CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; oxalyl dichloride; trimethylsilyl iodide; camphor-10-sulfonic acid; hydrogen; iodine; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 4.1: Swern oxidation / 18.1: Wittig olefination;

DOI:10.1016/j.tetlet.2006.07.027

upstream raw materials:

2-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-propenal

(carbethoxyethylidene)triphenylphosphorane

tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Downstream raw materials:

4-Bromo-benzoic acid (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-2-hydroxy-propyl ester

((2R,3R)-3-{1-[(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl]-vinyl}-2-methyl-oxiranyl)-methanol

(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[2-((2R,3R)-3-hydroxymethyl-3-methyl-oxiranyl)-allyl]-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

(R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol

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