(Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.0^2,12]pentadec-5-ene-3,7-diyn-14-one

Base Information

• Chemical Name: (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.0^2,12]pentadec-5-ene-3,7-diyn-14-one
• CAS No.: 122908-85-4
• Molecular Formula: C₂₀H₁₆O₃S
• Molecular Weight: 336.411

Synonyms:(Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.0^2,12]pentadec-5-ene-3,7-diyn-14-one

Chemical Property of (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.0^2,12]pentadec-5-ene-3,7-diyn-14-one

Chemical Property:

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Technology Process of (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.0^2,12]pentadec-5-ene-3,7-diyn-14-one

There total 7 articles about (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.0^2,12]pentadec-5-ene-3,7-diyn-14-one 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: 75.0%

(Z)-(1R,2R,9S,10S)-2-Hydroxy-13-oxo-1-phenylsulfanyl-bicyclo[7.2.2]tridec-5-ene-3,7-diyne-10-carboxylic acid methyl ester (122908-84-3) → (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.02,12]pentadec-5-ene-3,7-diyn-14-one (122908-85-4)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/S0040-4039(00)95220-1

Reference yield:

(Z)-(2S,9S,10S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-bicyclo[7.2.2]trideca-1(12),5-diene-3,7-diyne-10-carboxylic acid methyl ester → (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.02,12]pentadec-5-ene-3,7-diyn-14-one (122908-85-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NMO / tetrapropylammonium perruthenate

2: 93 percent / HF / acetonitrile

3: 90 percent / Et₃N / methanol

4: 75 percent / NaBH₄ / methanol

With sodium tetrahydroborate; N-methyl-2-indolinone; hydrogen fluoride; triethylamine; tetrapropylammonium perruthennate; In methanol; acetonitrile;

DOI:10.1016/S0040-4039(00)95220-1

Reference yield:

(2E,6Z,12E)-10-(tert-Butyl-dimethyl-silanyloxy)-13-(4-methoxy-benzyloxy)-11-methylene-trideca-2,6,12-triene-4,8-diynoic acid methyl ester (122908-80-9) → (Z)-(1S,2S,9R,10R,12R)-9-Hydroxy-10-phenylsulfanyl-13-oxa-tricyclo[8.4.1.02,12]pentadec-5-ene-3,7-diyn-14-one (122908-85-4)

Guidance literature:

Multi-step reaction with 6 steps

1: benzene / 80 °C

2: CAN or DDQ

3: NMO / tetrapropylammonium perruthenate

4: 93 percent / HF / acetonitrile

5: 90 percent / Et₃N / methanol

6: 75 percent / NaBH₄ / methanol

With sodium tetrahydroborate; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; hydrogen fluoride; triethylamine; tetrapropylammonium perruthennate; In methanol; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)95220-1

upstream raw materials:

(Z)-(1R,2R,9S,10S)-2-Hydroxy-13-oxo-1-phenylsulfanyl-bicyclo[7.2.2]tridec-5-ene-3,7-diyne-10-carboxylic acid methyl ester

thiophenol

(Z)-(2S,9S,10S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-oxo-bicyclo[7.2.2]trideca-1⁽¹²⁾,5-diene-3,7-diyne-10-carboxylic acid methyl ester

(2E,6Z,12E)-10-(tert-Butyl-dimethyl-silanyloxy)-13-(4-methoxy-benzyloxy)-11-methylene-trideca-2,6,12-triene-4,8-diynoic acid methyl ester

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