12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol

Base Information

Chemical Name:12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol
CAS No.:112358-28-8
Molecular Formula:C₃₁H₄₈O₇S
Molecular Weight:564.784
Hs Code.:

Synonyms:

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Chemical Property of 12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol

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Technology Process of 12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol

There total 10 articles about 12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol 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: 97.0%

: 112358-25-5,112358-27-7,131346-77-5,131346-83-3,131346-84-4,131347-89-2
12β-(1-ethoxyethoxy)picrasane-1α,3β-diol

: 98-59-9
p-toluenesulfonyl chloride

: 112358-28-8,131346-78-6,131346-85-5
12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol

Guidance literature:: With pyridine; at 0 ℃; for 48h;
DOI:10.1021/jo00003a039

Reference yield:

: 131250-81-2
12β-hydroxypicras-4-en-3-one

: 112358-28-8,131346-78-6,131346-85-5
12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 24 percent / Li/NH₃(liquid) / tetrahydrofuran / 0.67 h / -33 °C

3: 75 percent / CrO₃, pyridine / CH₂Cl₂ / 3 h

4: 96 percent / 0.5 M HCl / tetrahydrofuran / 3.5 h / Ambient temperature

5: 1) PhSeCl, TsOH, 2) pyridine, m-chloroperbenzoic acid / 1) ethyl acetate, 5 h, r.t., 2) 1 h, r.t.

6: 86 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

7: 86 percent / 2M aq. NaOH, 30percent H₂O₂ / tetrahydrofuran; methanol / 4 h / Ambient temperature

8: 1) LiAlH(tert.-BuO)3, 2) LiAlH₄ / 1) ether, 1 h at 0 deg C and 30 min at r.t., 2) THF, 1 h at 0 deg C and 2 h at r.t.

9: 97 percent / pyridine / 48 h / 0 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; Phenylselenyl chloride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00003a039

Reference yield:

: 131250-82-3,131250-86-7
12β-(1-ethoxyethoxy)picras-4-en-3-one

: 112358-28-8,131346-78-6,131346-85-5
12β-(1-ethoxyethoxy)-3β-(tosyloxy)picrasan-1α-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 24 percent / Li/NH₃(liquid) / tetrahydrofuran / 0.67 h / -33 °C

2: 75 percent / CrO₃, pyridine / CH₂Cl₂ / 3 h

3: 96 percent / 0.5 M HCl / tetrahydrofuran / 3.5 h / Ambient temperature

4: 1) PhSeCl, TsOH, 2) pyridine, m-chloroperbenzoic acid / 1) ethyl acetate, 5 h, r.t., 2) 1 h, r.t.

5: 86 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

6: 86 percent / 2M aq. NaOH, 30percent H₂O₂ / tetrahydrofuran; methanol / 4 h / Ambient temperature

7: 1) LiAlH(tert.-BuO)3, 2) LiAlH₄ / 1) ether, 1 h at 0 deg C and 30 min at r.t., 2) THF, 1 h at 0 deg C and 2 h at r.t.

8: 97 percent / pyridine / 48 h / 0 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; Phenylselenyl chloride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00003a039