[(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 924656-36-0
• Molecular Formula: C₃₆H₅₄O₆Si
• Molecular Weight: 610.907

Synonyms:[(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane

There total 20 articles about [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-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:

(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene → [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane (924656-36-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

3.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

4.1: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

5.1: TBAF / tetrahydrofuran / 2.5 h / 20 °C

6.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

7.1: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

8.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

9.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

10.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

11.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

12.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

12.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

13.1: 9-BBN / tetrahydrofuran / 20 °C

13.2: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 3 h / 20 °C

14.1: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

15.1: 263.7 mg / PPTS / CH₂Cl₂ / 1 h / 20 °C

16.1: t-BuOK / tetrahydrofuran / 0.33 h / 20 °C

16.2: n-Bu₄NI / tetrahydrofuran / 1 h / 20 °C

17.1: 171.6 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - 0 °C

18.1: I₂; imidazole; PPh₃ / benzene / 0.5 h / 20 °C

19.1: 462.2 mg / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; methanol; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; copper diacetate; pyridine-SO₃ complex; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; oxygen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; copper(I) bromide; palladium dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl acetamide; water; dimethyl sulfoxide; benzene; 4.1: Wacker-Tsuji reaction / 12.2: Wittig reaction;

DOI:10.1021/ja066772y

Reference yield:

(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-oxepan-3-ol (908866-07-9) → [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane (924656-36-0)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

2.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

3.1: 92 percent / PdCl₂; O₂; Cu(OAc)2 / H₂O; N,N-dimethyl-acetamide / 36 h / 20 °C

4.1: TBAF / tetrahydrofuran / 2.5 h / 20 °C

5.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

6.1: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

7.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

9.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

10.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

11.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

11.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

12.1: 9-BBN / tetrahydrofuran / 20 °C

12.2: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 3 h / 20 °C

13.1: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

14.1: 263.7 mg / PPTS / CH₂Cl₂ / 1 h / 20 °C

15.1: t-BuOK / tetrahydrofuran / 0.33 h / 20 °C

15.2: n-Bu₄NI / tetrahydrofuran / 1 h / 20 °C

16.1: 171.6 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - 0 °C

17.1: I₂; imidazole; PPh₃ / benzene / 0.5 h / 20 °C

18.1: 462.2 mg / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; methanol; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; copper diacetate; pyridine-SO₃ complex; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; oxygen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; copper(I) bromide; palladium dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; benzene; 3.1: Wacker-Tsuji reaction / 11.2: Wittig reaction;

DOI:10.1021/ja066772y

Reference yield:

4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-hydroxy-oxepan-2-yl)-butan-2-one (924656-67-7) → [(2R,3S,5aR,8R,10aS)-2-(3-Benzyloxy-propyl)-8-(4-methoxy-benzyloxy)-3-methyl-7-methylene-decahydro-1,6-dioxa-heptalen-3-yloxy]-tert-butyl-dimethyl-silane (924656-36-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 178.3 mg / 4-methylmorpholine / CH₂Cl₂ / 20 °C

2.1: 57 percent / SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

3.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4.1: Et₃N / CH₂Cl₂ / 3 h / 20 °C

5.1: 254.8 mg / CSA / methanol; CH₂Cl₂ / 1 h / 0 °C

6.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

7.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

7.2: 265.9 mg / tetrahydrofuran / 0.5 h / 0 °C

8.1: 9-BBN / tetrahydrofuran / 20 °C

8.2: aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 3 h / 20 °C

9.1: H₂ / Pd(OH)2/C / methanol / 1 h / 20 °C

10.1: 263.7 mg / PPTS / CH₂Cl₂ / 1 h / 20 °C

11.1: t-BuOK / tetrahydrofuran / 0.33 h / 20 °C

11.2: n-Bu₄NI / tetrahydrofuran / 1 h / 20 °C

12.1: 171.6 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - 0 °C

13.1: I₂; imidazole; PPh₃ / benzene / 0.5 h / 20 °C

14.1: 462.2 mg / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C

With 4-methyl-morpholine; 1H-imidazole; methanol; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; pyridine-SO₃ complex; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; benzene; 7.2: Wittig reaction;

DOI:10.1021/ja066772y

upstream raw materials:

((2R,4aR,6S,7R,9aS)-7-Benzyloxy-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol

(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-oxepan-3-ol

4-((2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-hydroxy-oxepan-2-yl)-butan-2-one

(1S,3R,7S,10R,12S,13R)-13-Benzyloxy-12-benzyloxymethyl-7-methyl-2,6,11-trioxa-tricyclo[8.5.0.0^3,7]pentadecan-5-one

Downstream raw materials:

C₆₆H₉₆O₉Si₂

C₅₈H₉₈O₉Si₃

C₆₀H₉₂O₉SSi₂

6-[7-(3-benzyloxy-propyl)-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-8-methyl-decahydro-1,6-dioxa-heptalen-2-ylmethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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