2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol

Base Information

• Chemical Name: 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol
• CAS No.: 724422-98-4
• Molecular Formula: C₃₈H₅₂O₄Si
• Molecular Weight: 600.914

Synonyms:2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol

Chemical Property of 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol

Chemical Property:

Purity/Quality:

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Technology Process of 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol

There total 16 articles about 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol 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:

(+-)-2-methyl-pent-4-enoic acid (1575-74-2) → 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol (724422-98-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: LiAlH₄ / tetrahydrofuran / 16 h / 20 °C

2.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

3.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

4.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

5.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

6.1: LiAlH₄ / diethyl ether / 0 - 20 °C

7.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

9.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

11.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

12.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

13.1: 98 percent / H₂ / Pd/C / ethanol / 0.08 h / 760 Torr

14.1: LiHMDS / ethanol / 1.5 h / 0 - 20 °C

15.1: 140 mg / LiAlH₄ / diethyl ether / 1.08 h / 0 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.2: Suzuki-Miyaura coupling / 4.1: Sharpless dihydroxylation / 12.1: Horner-Wadsworth-Emmons cyclization / 14.1: Wittig olefination;

DOI:10.1021/jo048115z

Reference yield:

2-methylpent-4-en-1-ol (5673-98-3) → 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol (724422-98-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

2.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

3.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

4.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

5.1: LiAlH₄ / diethyl ether / 0 - 20 °C

6.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

8.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

10.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

11.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

12.1: 98 percent / H₂ / Pd/C / ethanol / 0.08 h / 760 Torr

13.1: LiHMDS / ethanol / 1.5 h / 0 - 20 °C

14.1: 140 mg / LiAlH₄ / diethyl ether / 1.08 h / 0 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.2: Suzuki-Miyaura coupling / 3.1: Sharpless dihydroxylation / 11.1: Horner-Wadsworth-Emmons cyclization / 13.1: Wittig olefination;

DOI:10.1021/jo048115z

Reference yield:

tert-butyldipheny((2-methylpent-4-en-1-yl)oxy)silane (144693-95-8) → 2-{(E)-(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyloxepan-3-ylidene}ethanol (724422-98-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

1.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

2.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

3.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

4.1: LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

6.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

7.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

9.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

10.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

11.1: 98 percent / H₂ / Pd/C / ethanol / 0.08 h / 760 Torr

12.1: LiHMDS / ethanol / 1.5 h / 0 - 20 °C

13.1: 140 mg / LiAlH₄ / diethyl ether / 1.08 h / 0 - 20 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; lithium hexamethyldisilazane; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 1.2: Suzuki-Miyaura coupling / 2.1: Sharpless dihydroxylation / 10.1: Horner-Wadsworth-Emmons cyclization / 12.1: Wittig olefination;

DOI:10.1021/jo048115z

upstream raw materials:

(+-)-2-methyl-pent-4-enoic acid

2-methylpent-4-en-1-ol

tert-butyldipheny((2-methylpent-4-en-1-yl)oxy)silane

(Z)-ethyl 8-(tert-butyldiphenylsilanyloxy)-3,7-dimethyloct-2-enoate

Downstream raw materials:

(E)-{5-[(2S,3R)-3-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-2-methylpentyloxy}tert-butyldiphenylsilane

5-{(2S,3R)-3-Benzyloxy-6-[2-benzyloxy-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2-methyl-pentan-1-ol

5-{(2S,3R)-3-Benzyloxy-6-[2-benzyloxy-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2-methyl-pentanoic acid

(E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide

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