(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

Base Information

Chemical Name:(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol
CAS No.:131414-02-3
Molecular Formula:C₄₀H₅₆O₆SSi₂
Molecular Weight:721.118
Hs Code.:

(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

Synonyms:(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

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Chemical Property of (3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

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Technology Process of (3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

There total 22 articles about (3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-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: 82.0%

: 135419-86-2
<3R(E),3aR,4S,6S,7R,7aR>-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)vinyl>benzofuran-3a-ol

: 131414-02-3
(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 20h; Ambient temperature;

Reference yield: 80.0%

: 135419-87-3
<3S(E),3aR,4S,6S,7R,7aR)>-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)vinyl>benzofuran-3a-ol

: 131414-02-3
(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 3.5h; Ambient temperature;

Reference yield:

: 127785-52-8
2-bromo-4-phenylthiobut-1-ene

: 131414-02-3
(3E,3aS,4S,6S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-4-<(tert-butyldiphenylsilyloxy)methyl>octahydro-6-methyl-3-<2-(phenylsulphonyl)ethylidene>benzofuran-3a-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) tert-BuLi / 1.) pentane, ether, THF, -78 deg C, 5 min, 2.) -78 deg C, 5 min

2: 89 percent / oxone, pH 4 aqueous buffer / tetrahydrofuran; methanol / 2 h / Ambient temperature

3: 69 percent / tert-butyl hydroperoxide, vanadyl acetylacetonate / toluene; CH₂Cl₂ / Ambient temperature; 0 deg C to RT

4: 80 percent / 15percent aq. H₂SO₄ / tetrahydrofuran / 12 h / 60 °C

5: 91 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

6: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

7: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

8: 79 percent / NaBH₄ / methanol / Ambient temperature

9: 1.) borane methyl sulphide complex, 2.) H₂O₂, NaOH / 1.) THF, RT, 64 h, 2.) 0 deg C -> RT

10: 84 percent / toluene-p-sulphonyl chloride, pyridine / 14 h / Ambient temperature

11: 1.) tert-BuLi / 1.) hexane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min

12: 93 percent / 80percent m-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 0.25 h / Ambient temperature

13: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 3.5 h / Ambient temperature

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; Oxone; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide borane complex; pH 4 aqueous buffer; vanadyl acetylacetonate; sulfuric acid; dihydrogen peroxide; tert.-butyl lithium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;