3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

Base Information

Chemical Name:3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester
CAS No.:99457-79-1
Molecular Formula:C₂₅H₃₆O₈S
Molecular Weight:496.622
Hs Code.:

3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

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Chemical Property of 3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

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Technology Process of 3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

There total 13 articles about 3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester 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: 93.0%

: 98-59-9
p-toluenesulfonyl chloride

: 99457-78-0
3-((3aR,4aR,5R,6S,8aR,8bR)-5-Hydroxymethyl-2,2,6-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl)-propionic acid ethyl ester

: 99457-79-1
3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

Guidance literature:: With pyridine; for 2h;
DOI:10.1021/jo00350a063

Reference yield:

: (2R,3R,3aR,6S,7S,7aR)-7-(hydroxymethyl)-2,3-O-(isopropylidenedioxy)-6-methyl-6-(oxomethyl)octahydrobenzo<3,4-b>furan α,β-lactol

: 99457-79-1
3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / 2 h / 95 °C

2: 93 percent / imidazole / dimethylformamide / 0.5 h

3: 86 percent / aq. (CH₃COO)2Cu / tetrahydrofuran / 36 h / 70 °C

4: 1.) NaH / 1.) C₆H₆, 5 min, 2.) C₆H₆, reflux, 45 min

5: 96 percent / aq. H₂SO₄ / ethanol / 3 h / Ambient temperature

6: 83 percent / Celite, pyridinium dichromate / CH₂Cl₂ / 17 h

7: 68 percent / 4-(dimethylamino)pyridine, Et₃N / tetrahydrofuran / 48 h / 55 °C

8: 98 percent / H₂ / 5percent Pt/C / benzene / 0.5 h / 10343 Torr

9: 100 percent / EtONa / ethanol / 1 h

10: 93 percent / pyridine / 2 h

With pyridine; 1H-imidazole; dmap; dipyridinium dichromate; Celite; sulfuric acid; hydrogen; sodium ethanolate; copper diacetate; sodium hydride; triethylamine; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00350a063

Reference yield:

: 99457-69-9
(2R,3R,3aR,6S,7S,7aR)-7-<<(tert-butyldimethylsilyl)oxy>methyl>-2,3-(isopropylidenedioxy)-6-methyl-6-(oxomethyl)octahydrobenzo<3,4-b>furan

: 99457-79-1
3-[(3aR,4aR,5R,6S,8aR,8bR)-2,2,6-Trimethyl-5-(toluene-4-sulfonyloxymethyl)-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-6-yl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) C₆H₆, 5 min, 2.) C₆H₆, reflux, 45 min

2: 96 percent / aq. H₂SO₄ / ethanol / 3 h / Ambient temperature

3: 83 percent / Celite, pyridinium dichromate / CH₂Cl₂ / 17 h

4: 68 percent / 4-(dimethylamino)pyridine, Et₃N / tetrahydrofuran / 48 h / 55 °C

5: 98 percent / H₂ / 5percent Pt/C / benzene / 0.5 h / 10343 Torr

6: 100 percent / EtONa / ethanol / 1 h

7: 93 percent / pyridine / 2 h

With pyridine; dmap; dipyridinium dichromate; Celite; sulfuric acid; hydrogen; sodium ethanolate; sodium hydride; triethylamine; platinum on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; benzene;
DOI:10.1021/jo00350a063