(1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene

Base Information

• Chemical Name: (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene
• CAS No.: 188052-35-9
• Molecular Formula: C₂₈H₄₀O₂SSi
• Molecular Weight: 468.776

Synonyms:(1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene

Chemical Property of (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene

There total 16 articles about (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene 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: 88.0%

sodium thiophenolate (930-69-8) + ((1R,6S)-6-Benzyloxy-3-chloromethyl-1-methyl-cyclohex-2-enylmethoxy)-tert-butyl-dimethyl-silane (188052-34-8) → (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene (188052-35-9)

Guidance literature:

In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

((S)-2-Methoxy-1,5-dimethyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (115513-10-5) → (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene (188052-35-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 91 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature

2: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

3: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

4: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

5: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

6: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

7: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

8: Et₂NLi / diethyl ether / Heating

9: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

10: 98 percent / SOCl₂, pyridine / diethyl ether / 0.05 h / 0 °C

11: 88 percent / tetrahydrofuran / 1.5 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; lithium diethylamide; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(99)00305-1

Reference yield:

(2'S,2S)-2,4-dimethyl-2-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-3-cyclohexen-1-one (237406-10-9) → (1S,2R)-1-benzyl(oxy)-2-methyl-2-tert-butyldimethylsilyl(oxy)methyl-4-thiophenylmethyl-3-cyclohexene (188052-35-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / NaBH₄, ZnCl₂ / tetrahydrofuran / 1 h / -60 - -15 °C

2: 63 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.) room temp., 24 h, 2.) reflux, 3 d

3: 90 percent / I₂ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

4: 98 percent / DIBAL-H / CH₂Cl₂ / 1.) -10 deg C, 15 min, 2.) 0 deg C, 15 min

5: 99 percent / 1,5-diazabicyclo<5.4.0>undecene-5 / CH₂Cl₂ / 1 h / Ambient temperature

6: 94 percent / NaBH₄ / methanol / 0.5 h / Ambient temperature

7: Et₂NLi / diethyl ether / Heating

8: 95 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

9: 98 percent / SOCl₂, pyridine / diethyl ether / 0.05 h / 0 °C

10: 88 percent / tetrahydrofuran / 1.5 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; thionyl chloride; lithium diethylamide; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(99)00305-1

upstream raw materials:

thiophenol

((1R,6S)-6-Benzyloxy-3-chloromethyl-1-methyl-cyclohex-2-enylmethoxy)-tert-butyl-dimethyl-silane

sodium thiophenolate

benzyl bromide

Downstream raw materials:

(1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enecarbaldehyde

<(1R,2S)-1-methyl-2-benzyl(oxy)-5-thiophenylmethyl-5-cyclohexenyl>acetaldehyde

2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanone

2-((1S,6S)-6-Benzyloxy-1-methyl-3-phenylsulfanylmethyl-cyclohex-2-enyl)-1-((1R,5S,7S)-7-methoxy-2,2,4-trimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-3-yl)-ethanol

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