(3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol

Base Information

• Chemical Name: (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol
• CAS No.: 197520-84-6
• Molecular Formula: C₁₄H₁₈O₂S
• Molecular Weight: 250.362
• Mol file: 197520-84-6.mol

Synonyms:(3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol

Chemical Property of (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol

There total 13 articles about (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol 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: 93.0%

(4R,6S)-6-Methoxymethoxy-8-phenylsulfanyl-oct-1-yn-4-ol (197520-83-5) → (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol (197520-84-6)

Guidance literature:

With hydrogenchloride; In methanol; Heating;

DOI:10.1055/s-1997-1550

Reference yield:

(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate (197520-87-9) → (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol (197520-84-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 91 percent / H₂ / Lindlar cat. / toluene / Ambient temperature

2: 88 percent / p-TsOH / toluene / Heating

3: 88 percent / 30percent hydrogen peroxide, 6 N sodium hydroxide / methanol / 0 °C

4: 83 percent / diphenyl diselenide, sodium borohydride, AcOH / ethanol

5: 95 percent / imidazole / dimethylformamide / Ambient temperature

6: 83 percent / lithium borohydride / tetrahydrofuran / 0 - 20 °C

7: 90 percent / tributylphosphine / pyridine / Ambient temperature

8: 96 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

9: 71 percent / boron tribromide / CH₂Cl₂ / -30 °C

10: 97 percent / sodium hydroxide / tetrahydrofuran / Ambient temperature

11: 92 percent / i-Pr₂NEt / tetrahydrofuran / Ambient temperature

12: 93 percent / dimethylsulfoxide / Ambient temperature

13: 93 percent / conc. HCl / methanol / Heating

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; tributylphosphine; diphenyl diselenide; hydrogen; dihydrogen peroxide; boron tribromide; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-1997-1550

Reference yield:

(R)-6-Benzyloxymethyl-5,6-dihydro-2-pyrone (120996-46-5) → (3S,5R)-1-Phenylsulfanyl-oct-7-yne-3,5-diol (197520-84-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / 30percent hydrogen peroxide, 6 N sodium hydroxide / methanol / 0 °C

2: 83 percent / diphenyl diselenide, sodium borohydride, AcOH / ethanol

3: 95 percent / imidazole / dimethylformamide / Ambient temperature

4: 83 percent / lithium borohydride / tetrahydrofuran / 0 - 20 °C

5: 90 percent / tributylphosphine / pyridine / Ambient temperature

6: 96 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

7: 71 percent / boron tribromide / CH₂Cl₂ / -30 °C

8: 97 percent / sodium hydroxide / tetrahydrofuran / Ambient temperature

9: 92 percent / i-Pr₂NEt / tetrahydrofuran / Ambient temperature

10: 93 percent / dimethylsulfoxide / Ambient temperature

11: 93 percent / conc. HCl / methanol / Heating

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; tributylphosphine; diphenyl diselenide; dihydrogen peroxide; boron tribromide; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-1550

upstream raw materials:

(4R,6S)-6-Methoxymethoxy-8-phenylsulfanyl-oct-1-yn-4-ol

(R)-6-Benzyloxymethyl-5,6-dihydro-2-pyrone

(1S,4R,6S)-4-Benzyloxymethyl-3,7-dioxa-bicyclo[4.1.0]heptan-2-one

(4S,6R)-6-Benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-one

Downstream raw materials:

[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-oct-7-yne-1-sulfinyl]-benzene

[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-oct-7-ynylsulfanyl]-benzene