(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

Base Information

Chemical Name:(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol
CAS No.:215120-33-5
Molecular Formula:C₅₀H₈₄O₇SSi₂
Molecular Weight:885.45
Hs Code.:

(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

Synonyms:(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

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Chemical Property of (Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

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Technology Process of (Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

There total 8 articles about (Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol 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:

: 162718-31-2
((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

: 215120-33-5
(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

2: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

3: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

4: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / dimethylformamide / 0 °C

7: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

8: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja982431b

Reference yield:

: ((2S,3R,4S,6S)-4-Benzyloxy-6-formyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

: 215120-33-5
(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

2: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

3: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: imidazole / dimethylformamide / 0 °C

6: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

7: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

With 1H-imidazole; lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja982431b

Reference yield:

: 215120-31-3
[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

: 215120-33-5
(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: imidazole / dimethylformamide / 0 °C

4: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

5: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

With 1H-imidazole; lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja982431b