((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Base Information

• Chemical Name: ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)
• CAS No.: 1266251-35-7
• Molecular Formula: C₂₆H₅₀O₄Si₂
• Molecular Weight: 482.852

Synonyms:((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Chemical Property of ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

There total 9 articles about ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) 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: 95.0%

(1S,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol (1266251-34-6) + t-butyldimethylsiyl triflate (69739-34-0) → ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) (1266251-35-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 0.166667h; Inert atmosphere; Cooling with ice;

DOI:10.1007/s12039-010-0066-z

Reference yield:

(6S)-6-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]octa-1,7-dien-4-ol (921770-78-7) → ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) (1266251-35-7)

Guidance literature:

Multi-step reaction with 10 steps

1: Grubbs catalyst first generation / dichloromethane / 6 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: lithium hydrochloride monohydrate / methanol / 3 h / -5 °C / Inert atmosphere

5: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

6: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

7: sodium tetrahydroborate; CeCl₃H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

8: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

9: lithium hydrochloride monohydrate / methanol / 1 h / 0 °C / Inert atmosphere

10: 2,6-dimethylpyridine / dichloromethane / 0.17 h / Inert atmosphere; Cooling with ice

With 2,6-dimethylpyridine; Grubbs catalyst first generation; dmap; sodium tetrahydroborate; CeCl₃H₂O; lithium hydrochloride monohydrate; di-isopropyl azodicarboxylate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 8: Mitsunobu reaction;

DOI:10.1007/s12039-010-0066-z

Reference yield:

(S)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-3-enyl acetate (1266251-28-8) → ((1S,4S,5R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) (1266251-35-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: lithium hydrochloride monohydrate / methanol / 3 h / -5 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

5: sodium tetrahydroborate; CeCl₃H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7: lithium hydrochloride monohydrate / methanol / 1 h / 0 °C / Inert atmosphere

8: 2,6-dimethylpyridine / dichloromethane / 0.17 h / Inert atmosphere; Cooling with ice

With 2,6-dimethylpyridine; sodium tetrahydroborate; CeCl₃H₂O; lithium hydrochloride monohydrate; di-isopropyl azodicarboxylate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 6: Mitsunobu reaction;

DOI:10.1007/s12039-010-0066-z

upstream raw materials:

(6S)-6-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]octa-1,7-dien-4-ol

(1S,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

t-butyldimethylsiyl triflate

C₂₇H₃₉NO₇Si

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