Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

Base Information

Chemical Name:Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester
CAS No.:78668-80-1
Molecular Formula:C₃₃H₄₈O₉S₃
Molecular Weight:684.937
Hs Code.:

Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

Synonyms:Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

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Chemical Property of Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

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Technology Process of Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

There total 31 articles about Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl 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%

: 78668-79-8,89888-60-8,89888-61-9
(Z)-7-[(2R,3S,4R,6S)-2-((E)-3-Hydroxy-oct-1-enyl)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-tetrahydro-thiopyran-3-yl]-hept-5-enoic acid methyl ester

: 98-88-4
benzoyl chloride

: 78668-80-1
Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

Guidance literature:: With pyridine; In dichloromethane; 1.) 0 deg C, 1 h, 2.) r.t., 30 min;
DOI:10.1016/S0040-4020(01)88651-8

Reference yield:

: 78668-57-2
6-chloro-1-iodo-2-hexyne

: 78668-80-1
Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 77 percent / NaOMe / methanol / 25 deg C -> reflux

2: 1.) NaBH₄, 2.) diisobutylaluminum hydride / 1.) methanol, -55 deg C; 2.) toluene, -78 deg C

3: pyridine / CH₂Cl₂ / 25 °C

4: HMPA / 25 °C

5: 1.) aq. NaOH / 1.) reflux

6: H₂ / Lindlar catalyst

7: pyridine / CH₂Cl₂ / 0 °C

8: Et₃N / -20 °C

9: 1.) NaOMe, MeOH, 2.) Collins reagent, 3.) DBU

10: HMPA, TMEDA / tetrahydrofuran / -78 °C

11: Collins reagent / -20 °C

12: 5 percent / H₂S, NaOAc / ethanol / Heating

13: 78 percent / diisopropylethylamine / dimethylformamide / 25 °C

14: NaBH₄ / ethanol / 0 °C

15: p-toluenesulfonic acid / acetone / 0 °C

16: diethyl ether / 25 °C

18: NaBH₄

With pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; Collins oxidation agent; hydrogen sulfide; hydrogen; sodium methylate; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja00405a059

Reference yield:

: 78668-60-7
2-(6-Chloro-hex-2-ynyl)-4,4-dimethoxy-butane-1,3-diol

: 78668-80-1
Benzoic acid 1-{(E)-2-[(2S,3R,4S,6R)-4-methanesulfonyloxy-6-(2-methoxycarbonyl-ethylsulfanyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-thiopyran-2-yl]-vinyl}-hexyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: pyridine / CH₂Cl₂ / 25 °C

2: HMPA / 25 °C

3: 1.) aq. NaOH / 1.) reflux

4: H₂ / Lindlar catalyst

5: pyridine / CH₂Cl₂ / 0 °C

6: Et₃N / -20 °C

7: 1.) NaOMe, MeOH, 2.) Collins reagent, 3.) DBU

8: HMPA, TMEDA / tetrahydrofuran / -78 °C

9: Collins reagent / -20 °C

10: 5 percent / H₂S, NaOAc / ethanol / Heating

11: 78 percent / diisopropylethylamine / dimethylformamide / 25 °C

12: NaBH₄ / ethanol / 0 °C

13: p-toluenesulfonic acid / acetone / 0 °C

14: diethyl ether / 25 °C

16: NaBH₄

With pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; Collins oxidation agent; hydrogen sulfide; hydrogen; sodium methylate; sodium acetate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja00405a059