(1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

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Chemical Name:(1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne
CAS No.:138914-94-0
Molecular Formula:C₃₈H₆₈O₃Si₂
Molecular Weight:629.127
Hs Code.:

Synonyms:(1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

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Chemical Property of (1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

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Technology Process of (1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

There total 9 articles about (1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne 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: 94.0%

: 116506-67-3
TB

: 138914-92-8
de-A,B-24-oxacholest-8-en-8-yl trifluoromethanesulfonate

: 138914-94-0
(1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

Guidance literature:: With triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 75 ℃; for 20h;
DOI:10.1016/S0040-4020(01)86275-X

Reference yield:

: 55812-82-3,63730-57-4,63730-58-5,102281-42-5
(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol

: 138914-94-0
(1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / i-Pr₂NH, 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: 1) O₃, pyridine, 2) NaBH₄ / 1) MeOH, CH₂Cl₂, -78 deg C, 30 min, 2) rt, 4 h

3: 90 percent / pyridine / 72 h / 4 °C

4: 95 percent / dimethylsulfoxide / 4 h / 90 °C

6: 1) NaH / 1) DMF, hexane, 1 h, rt, 2) 24 h

7: 97 percent / AG 50W-X₄ / methanol / 96 h

8: 98 percent / pyridinium dichromate, pyridinium tosylate / CH₂Cl₂ / 12 h

9: 1) i-Pr₂NLi / 1) THF, hexane, a)-78 deg C, 15 min, b)rt, 90 min, 2) THF, a) -78 deg C to rt, b) rt, 10 h

10: 94 percent / Et₃N / Pd(Ph₃P)2Cl₂ / dimethylformamide / 20 h / 75 °C

With pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; AG 50W-X₄; pyridinium p-toluenesulfonate; sodium hydride; ozone; triethylamine; diisopropylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86275-X

Reference yield:

: 147833-08-7
(8β)-de-A,B-8-methoxymethyloxy-23,24-dinorcholan-22-ol

: 138914-94-0
(1α,3β)-1,3-bis(t-butyldimethylsilyloxy)-24-oxa-9,10-secocholesta-5(10),8-dien-6-yne

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / pyridine / 72 h / 4 °C

2: 95 percent / dimethylsulfoxide / 4 h / 90 °C

4: 1) NaH / 1) DMF, hexane, 1 h, rt, 2) 24 h

5: 97 percent / AG 50W-X₄ / methanol / 96 h

6: 98 percent / pyridinium dichromate, pyridinium tosylate / CH₂Cl₂ / 12 h

7: 1) i-Pr₂NLi / 1) THF, hexane, a)-78 deg C, 15 min, b)rt, 90 min, 2) THF, a) -78 deg C to rt, b) rt, 10 h

8: 94 percent / Et₃N / Pd(Ph₃P)2Cl₂ / dimethylformamide / 20 h / 75 °C

With pyridine; dipyridinium dichromate; AG 50W-X₄; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86275-X