(1S,3R,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane
• CAS No.: 90580-78-2
• Molecular Formula: C₁₅H₂₀O₄S
• Molecular Weight: 296.387

Synonyms:(1S,3R,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property of (1S,3R,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

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Technology Process of (1S,3R,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

There total 19 articles about (1S,3R,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane 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: 92.0%

(2R*,4R*,5R*)-(+/-)-4-(Brommethyl)-5-ethyl-2-methyl-2-<2-(phenylsulfonyl)ethyl>-1,3-dioxolan (89635-24-5) + lithium diisopropyl amide (4111-54-0) → (1RS,3SR,5SR,7SR)-7-Ethyl-5-methyl-3-phenylsulfonyl-6,8-dioxabicyclo<3.2.1>octan (85785-84-8,89675-65-0,90580-78-2,90580-79-3,95721-84-9,117180-78-6,117180-79-7,124265-35-6,124265-36-7)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

Reference yield: 76.0%

Toluene-4-sulfonic acid (1R,5R,7R)-3-benzenesulfonyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester (85800-96-0,90580-77-1,95721-85-0) → 3-phenylsulfonyl-exo-brevicomin (85785-84-8,89675-65-0,90580-78-2,90580-79-3,95721-84-9,117180-78-6,117180-79-7,124265-35-6,124265-36-7)

Guidance literature:

In diethyl ether; at -20 - 20 ℃; for 5h;

DOI:10.1016/S0040-4039(00)85892-X

Reference yield: 37.0%

(+/-)-4-ethyl-2,2-dimethyl-5-<3-(2-methyl-1,3-dioxolan-2-yl)-2-(phenylsulfonyl)propyl>-1,3-dioxolan (117120-82-8) → (+/-)-exo-7-ethyl-5-methyl-endo-3-phenylsulfonyl-6,8-dioxabicyclo<3.2.1>octan (85785-84-8,89675-65-0,90580-78-2,90580-79-3,95721-84-9,117180-78-6,117180-79-7,124265-35-6,124265-36-7) + (+/-)-exo-7-ethyl-5-methyl-exo-3-phenylsulfonyl-6,8-dioxobicyclo<3.2.1>octan (85785-84-8,89675-65-0,90580-78-2,90580-79-3,95721-84-9,117180-78-6,117180-79-7,124265-35-6,124265-36-7)

Guidance literature:

With water; toluene-4-sulfonic acid; In benzene; for 18h; Heating;

upstream raw materials:

(+/-)-4-ethyl-2,2-dimethyl-5-<3-(2-methyl-1,3-dioxolan-2-yl)-2-(phenylsulfonyl)propyl>-1,3-dioxolan

Toluene-4-sulfonic acid (1R,5R,7R)-3-benzenesulfonyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester

4-phenylsulfanyl-butan-2-one

[(4R,5R)-5-Hydroxymethyl-2-methyl-2-(2-phenylsulfanyl-ethyl)-[1,3]dioxolan-4-yl]-methanol

Downstream raw materials:

(1S,5R,7S)-3-Benzenesulfonyl-7-ethyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]octane

(1S,5R,7S)-7-Ethyl-5-methyl-3-phenylsulfanyl-6,8-dioxa-bicyclo[3.2.1]octane

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