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

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Chemical Name: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
CAS No.:370884-94-9
Molecular Formula:C₃₃H₅₀O₇Si
Molecular Weight:586.841
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 21 articles about 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 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:

: 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-ol

: 370884-94-9
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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

: 250226-93-8
(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

: 370884-94-9
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

Guidance literature:: Multi-step reaction with 20 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

18.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

18.2: 86 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

19.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

20.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

20.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

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; diethyl ether; 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 / 18.1: Swern oxidation / 20.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 116237-17-3
4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

: 370884-94-9
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

Guidance literature:: Multi-step reaction with 19 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

17.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

17.2: 86 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

18.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

19.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

19.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

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; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization / 14.1: Swern oxidation / 15.2: Wittig reaction / 17.1: Swern oxidation / 19.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X