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

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Chemical Name:1-methyl-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane-2-exo,3-exo-dimethanol
CAS No.:117626-65-0
Molecular Formula:C₁₆H₂₁ClO₄S
Molecular Weight:344.859
Hs Code.:

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

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

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

There total 7 articles about 1-methyl-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane-2-exo,3-exo-dimethanol 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: 80.0%

: 67-56-1
methanol

: 117626-64-9
4-methyl-5-(phenylthio)-7-oxabicyclo<2.2.1>hept-5-ene-2-exo,3-exo-dimethanol

: 117626-65-0
1-methyl-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane-2-exo,3-exo-dimethanol

Guidance literature:: With N-chloro-succinimide; In methanol; at 25 ℃; for 0.25h;
DOI:10.1021/jo00262a024

Reference yield:

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

: 117626-65-0
1-methyl-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane-2-exo,3-exo-dimethanol

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

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

: 117626-65-0
1-methyl-5-exo-methoxy-5-endo-(phenylthio)-6-exo-chloro-7-oxabicyclo<2.2.1>heptane-2-exo,3-exo-dimethanol

Guidance literature:: Multi-step reaction with 6 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

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