2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol

Base Information

• Chemical Name: 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol
• CAS No.: 370884-57-4
• Molecular Formula: C₃₂H₅₀O₇Si
• Molecular Weight: 574.83

Synonyms:2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol

Chemical Property of 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol

There total 18 articles about 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol 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: 84.0%

tert-Butyl-[(2R,3S,6R,7S)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-vinyl-oxepan-3-yloxy]-dimethyl-silane (370884-91-6) → 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol (370884-57-4)

Guidance literature:

tert-Butyl-[(2R,3S,6R,7S)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-vinyl-oxepan-3-yloxy]-dimethyl-silane; With bis(cyclohexanyl)borane; at 0 ℃;

With sodium hydroxide; dihydrogen peroxide; at 0 ℃;

DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester (250226-93-8) → 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol (370884-57-4)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

5.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

6.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

8.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

9.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

10.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

10.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

11.1: 77 percent / KH / tetrahydrofuran / 1 h / 20 °C

12.1: 84 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 27 h / 20 °C

13.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

14.1: 91 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.5 h / 0 °C

15.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

15.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

16.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

16.2: 91 percent / tetrahydrofuran / 1 h

17.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

17.2: 84 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0.5 h

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 5.1: Yamaguchi lactonization / 15.1: Swern oxidation / 16.2: Wittig reaction;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → 2-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-ethanol (370884-57-4)

Guidance literature:

Multi-step reaction with 16 steps

1.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

4.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

5.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

7.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

9.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

9.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

10.1: 77 percent / KH / tetrahydrofuran / 1 h / 20 °C

11.1: 84 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 27 h / 20 °C

12.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

13.1: 91 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.5 h / 0 °C

14.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

14.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

15.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

15.2: 91 percent / tetrahydrofuran / 1 h

16.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

16.2: 84 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0.5 h

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; cyclohexene; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization / 14.1: Swern oxidation / 15.2: Wittig reaction;

DOI:10.1016/S0040-4020(02)00039-X

upstream raw materials:

tert-Butyl-[(2R,3S,6R,7S)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-vinyl-oxepan-3-yloxy]-dimethyl-silane

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

p-methoxybenzyl chloride

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

Downstream raw materials:

1-[(2R,3S,6R,7S)-3-Hydroxy-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-propan-2-one

1-[(2R,3S,6R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-propan-2-one

3-[(2R,3S,4aR,6S,7R,9aS)-3-Hydroxy-7-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-3,4a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-propionaldehyde

(4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

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