1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

Base Information

Chemical Name:1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane
CAS No.:117626-67-2
Molecular Formula:C₁₆H₁₇ClO₂S
Molecular Weight:308.829
Hs Code.:

Synonyms:1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

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Chemical Property of 1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

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Technology Process of 1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

There total 9 articles about 1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane 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:

: 117626-66-1
Methanesulfonic acid (1R,2S,3R,4S,5S,6S)-5-chloro-3-methanesulfonyloxymethyl-6-methoxy-1-methyl-6-phenylsulfanyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl ester

: 117626-67-2
1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

Guidance literature:: With potassium tert-butylate; In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; at 0 ℃; for 13h; Yield given;
DOI:10.1021/jo00262a024

Reference yield:

: 56161-48-9
2-<2-(phenylthio)ethyl>-1,3-dioxolane

: 117626-67-2
1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 9 steps

1: N-chlorosuccinimide / CCl₄ / 3 h / 25 °C

2: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C

3: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C

4: d-camphorsulfonic acid / methanol / 2 h / 25 °C

5: CHCl₃ / 12 h / 25 °C

6: LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

7: 80 percent / N-chlorosuccinimide / methanol / 0.25 h / 25 °C

8: triethylamine / tetrahydrofuran / 2 h / 0 °C

9: potassium tert-butoxide / hexamethylphosphoric acid triamide; dimethylformamide / 13 h / 0 °C

With N-chloro-succinimide; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; sec.-butyllithium; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00262a024

Reference yield:

: 117626-71-8
(+/-)-2-<2-chloro-2-(phenylthio)ethyl>-1,3-dioxolane

: 117626-67-2
1-methyl-2,3-bis(methylene)-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 8 steps

1: potassium tert-butoxide / tetrahydrofuran / 4.5 h / 25 °C

2: 1.) sec-butyllithium / 1.) DME, cyclohexane, from -78 deg C to -40 deg C, 15 min, 2.) from -78 deg C to 0 deg C

3: d-camphorsulfonic acid / methanol / 2 h / 25 °C

4: CHCl₃ / 12 h / 25 °C

5: LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

6: 80 percent / N-chlorosuccinimide / methanol / 0.25 h / 25 °C

7: triethylamine / tetrahydrofuran / 2 h / 0 °C

8: potassium tert-butoxide / hexamethylphosphoric acid triamide; dimethylformamide / 13 h / 0 °C

With N-chloro-succinimide; lithium aluminium tetrahydride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; sec.-butyllithium; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jo00262a024