dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester

Base Information

• Chemical Name: dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester
• CAS No.: 350046-08-1
• Molecular Formula: C₅₄H₇₆O₆S₂Si₂
• Molecular Weight: 941.497

Synonyms:dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester

Chemical Property of dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester

Chemical Property:

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Technology Process of dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester

There total 19 articles about dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl 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: 98.0%

carbon disulfide (75-15-0,12122-00-8) + (E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-en-1-ol (350046-07-0) + methyl iodide (74-88-4) → dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester (350046-08-1)

Guidance literature:

carbon disulfide; (E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-en-1-ol; With potassium hydride; In diethyl ether; at 20 ℃;

methyl iodide; at 20 ℃;

DOI:10.1016/S0040-4039(01)00530-5

Reference yield:

(2S,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxirane-2-carbaldehyde (131310-58-2) → dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester (350046-08-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 89 percent / PhCO₂H / benzene / 20 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 20 °C

3.1: 78 percent / PPTS / CH₂Cl₂ / 20 °C

4.1: 95 percent / hydrogen / Pd/C / methanol / 20 °C

5.1: 91 percent / LiAlH₄ / diethyl ether / 0 °C

6.1: 90 percent / KH / tetrahydrofuran / 0 °C

7.1: 91 percent / CSA; MeOH / CH₂Cl₂ / 20 °C

8.1: 96 percent / imidazole / dimethylformamide / 70 °C

9.1: 92 percent / CSA; MeOH / CH₂Cl₂ / 0 °C

10.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

10.2: 89 percent / Et₃N / -78 - 20 °C

11.1: 76 percent / t-BuLi / diethyl ether / -78 °C

12.1: KH / diethyl ether / 20 °C

12.2: 98 percent / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hydride; dimethyl sulfoxide; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Wittig reaction / 10.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00530-5

Reference yield:

(E)-3-[(2R,3R)-3-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-ylmethyl)-2-methyl-oxiranyl]-acrylic acid methyl ester (350045-95-3) → dithiocarbonic acid O-[1-[5-benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-enyl] ester S-methyl ester (350046-08-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 78 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 95 percent / hydrogen / Pd/C / methanol / 20 °C

3.1: 91 percent / LiAlH₄ / diethyl ether / 0 °C

4.1: 90 percent / KH / tetrahydrofuran / 0 °C

5.1: 91 percent / CSA; MeOH / CH₂Cl₂ / 20 °C

6.1: 96 percent / imidazole / dimethylformamide / 70 °C

7.1: 92 percent / CSA; MeOH / CH₂Cl₂ / 0 °C

8.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

8.2: 89 percent / Et₃N / -78 - 20 °C

9.1: 76 percent / t-BuLi / diethyl ether / -78 °C

10.1: KH / diethyl ether / 20 °C

10.2: 98 percent / 20 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hydride; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 8.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)00530-5

upstream raw materials:

carbon disulfide

(E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-pent-2-en-1-ol

methyl iodide

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

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