(2S,4S,6S,8R,9S)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

Base Information

Chemical Name:(2S,4S,6S,8R,9S)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol
CAS No.:105989-32-0
Molecular Formula:C₂₃H₃₄O₅S
Molecular Weight:422.586
Hs Code.:

Synonyms:

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Chemical Property of (2S,4S,6S,8R,9S)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

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Technology Process of (2S,4S,6S,8R,9S)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

There total 61 articles about (2S,4S,6S,8R,9S)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-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:

: 104629-71-2
(R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol

: 105989-32-0,106037-28-9
(2S,4S,6S,8R,9S)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 80 percent / NBS, PPh₃ / CH₂Cl₂

2: 71 percent / dimethylformamide

3: 99 percent / NaOH, MeOH

4: 82 percent / PCC, molecular sieves 3A / CH₂Cl₂

5: 45 percent / LDA / tetrahydrofuran / -78 °C

6: 62 percent / p-TsOH / methanol / 5 h / Ambient temperature

7: n-Bu₄NF (tetrabutylammonium fluoride) / tetrahydrofuran / 12 h / Ambient temperature

8: H₂ / Lindlar cat. (Pd/CaCO₃/Pb) / toluene

9: DL-CSA (camphorsulfonic acid) / CH₂Cl₂

10: Collin's oxidation

11: LiAlH₄ / diethyl ether / -78 °C

With methanol; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; pyridinium chlorochromate; lithium diisopropyl amide; Lindlar's catalyst; DL-10-camphorsulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85191-6

Reference yield:

: 104629-71-2
(R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol

: 105989-32-0,106037-28-9
(2S,6S,8R)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / NBS, PPh₃ / CH₂Cl₂

2: 71 percent / dimethylformamide

3: 99 percent / NaOH, MeOH

4: 82 percent / PCC, molecular sieves 3A / CH₂Cl₂

5: 45 percent / LDA / tetrahydrofuran / -78 °C

6: 62 percent / p-TsOH / methanol / 5 h / Ambient temperature

7: n-Bu₄NF (tetrabutylammonium fluoride) / tetrahydrofuran / 12 h / Ambient temperature

8: H₂ / Lindlar cat. (Pd/CaCO₃/Pb) / toluene

9: DL-CSA (camphorsulfonic acid) / CH₂Cl₂

With methanol; sodium hydroxide; N-Bromosuccinimide; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; pyridinium chlorochromate; lithium diisopropyl amide; Lindlar's catalyst; DL-10-camphorsulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85191-6

Reference yield:

: 104629-71-2
(R)-(3-tert-butyldimethylsiloxy)-5-(pivaloyloxy)-1-pentanol

: 105989-32-0,106037-28-9
(2S,4R,6S,8R,9R)-8-((S)-sec-Butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 80 percent / NBS, PPh₃ / CH₂Cl₂

2: 71 percent / dimethylformamide

3: 99 percent / NaOH, MeOH

4: 82 percent / PCC, molecular sieves 3A / CH₂Cl₂

5: 45 percent / LDA / tetrahydrofuran / -78 °C

6: 62 percent / p-TsOH / methanol / 5 h / Ambient temperature

7: n-Bu₄NF (tetrabutylammonium fluoride) / tetrahydrofuran / 12 h / Ambient temperature

8: H₂ / Lindlar cat. (Pd/CaCO₃/Pb) / toluene

9: DL-CSA (camphorsulfonic acid) / CH₂Cl₂

10: Collin's oxidation

11: LiAlH₄ / diethyl ether / -78 °C

With methanol; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; pyridinium chlorochromate; lithium diisopropyl amide; Lindlar's catalyst; DL-10-camphorsulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)85191-6