(2S,3R,4aR,11S,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

Base Information

Chemical Name:(2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine
CAS No.:139025-45-9
Molecular Formula:C₃₀H₃₁NO₇S
Molecular Weight:549.645
Hs Code.:

Synonyms:(2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

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Chemical Property of (2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

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Technology Process of (2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

There total 18 articles about (2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine 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: 82.5%

: 1125-88-8
benzaldehyde dimethyl acetal

: 144609-79-0
(2S*,3R*,4aR*,11S*,11aR*)-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

: 139025-45-9
(2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

Guidance literature:: With toluene-4-sulfonic acid; In chloroform; for 1.33333h; Ambient temperature;
DOI:10.1021/jo00052a051

Reference yield:

: 17680-04-5
(3,4-methylenedioxy)phenylmagnesium bromide

: 139025-45-9
(2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

Guidance literature:: Multi-step reaction with 13 steps

1: 95.6 percent / tetrahydrofuran / 0.17 h / ice-cooling

2: 1) Et₃N, ethyl chloroformate, 2) NaN₃ / 1) acetone, ice-cooling, 0.5 h, 2) acetone, water, ice-cooling, 1 h

3: 16 h / Heating

4: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

5: Et₃N / CHCl₃ / 1 h / Ambient temperature

6: 100 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane / 2 h / Ambient temperature

7: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature

8: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h

9: 1) BH₃*THF, 2) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min

10: 100 percent / pyridine / 1 h / Ambient temperature

11: 80.6 percent / methanesulfonic acid, Ac₂O / 1,2-dichloro-ethane / 2 h / Ambient temperature

12: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature

13: 82.5 percent / p-TsOH*H₂O / CHCl₃ / 1.33 h / Ambient temperature

With pyridine; sodium hydroxide; sodium azide; borane-THF; methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; chloroformic acid ethyl ester; acetic anhydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; dmap; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; 1,2-dichloro-ethane;
DOI:10.1021/jo00052a051

Reference yield:

: 139025-42-6
(1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenyl-N-tosylamide

: 139025-45-9
(2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / N-methylmorpholine N-oxide / OsO₄ / dioxane / 2 h / Ambient temperature

2: 92.7 percent / pyridine / DMAP / 2 h / Ambient temperature

3: 1) t-BuOK / 1) THF, room temperature, 0.5 h, 2) room temperature, 2 h

4: 1) BH₃*THF, 2) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1) THF, ice-cooling, 4 h, 2) water, room temperature, 40 min

5: 100 percent / pyridine / 1 h / Ambient temperature

6: 80.6 percent / methanesulfonic acid, Ac₂O / 1,2-dichloro-ethane / 2 h / Ambient temperature

7: 100 percent / NaOMe / methanol / 0.33 h / Ambient temperature

8: 82.5 percent / p-TsOH*H₂O / CHCl₃ / 1.33 h / Ambient temperature

With pyridine; sodium hydroxide; borane-THF; methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium methylate; acetic anhydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; dmap; osmium(VIII) oxide; In 1,4-dioxane; methanol; chloroform; 1,2-dichloro-ethane;
DOI:10.1021/jo00052a051