((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Base Information

• Chemical Name: ((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)
• CAS No.: 1266251-39-1
• Molecular Formula: C₂₅H₅₄O₃Si₃
• Molecular Weight: 486.958

Synonyms:((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Chemical Property of ((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)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-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane)

There total 11 articles about ((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)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: 85.0%

(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol (1266251-38-0) + t-butyldimethylsiyl triflate (69739-34-0) → ((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) (1266251-39-1)

Guidance literature:

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

DOI:10.1007/s12039-010-0066-z

Reference yield:

(R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)-7-oxabicyclo[4.1.0]heptan-3-ol (1266546-06-8) → ((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) (1266251-39-1)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

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

6: acetic acid / water / 4 h / 70 °C / Inert atmosphere

7: sodium periodate / methanol; water / 0.5 h / Inert atmosphere; Cooling with ice

8: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

9: 2,6-dimethylpyridine / dichloromethane; N,N-dimethyl-formamide / 0.17 h / Inert atmosphere; Cooling with ice

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; CeCl₃H₂O; lithium hydrochloride monohydrate; di-isopropyl azodicarboxylate; Dess-Martin periodane; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

DOI:10.1007/s12039-010-0066-z

Reference yield:

(R)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)-7-oxabicyclo[4.1.0]heptan-3-yl acetate (1266546-07-9) → ((1S,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-ene-1,4-diyl)bis(oxy)bis(tert-butyldimethylsilane) (1266251-39-1)

Guidance literature:

Multi-step reaction with 10 steps

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

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

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

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

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

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

7: acetic acid / water / 4 h / 70 °C / Inert atmosphere

8: sodium periodate / methanol; water / 0.5 h / Inert atmosphere; Cooling with ice

9: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

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

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; CeCl₃H₂O; lithium hydrochloride monohydrate; di-isopropyl azodicarboxylate; Dess-Martin periodane; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5: Mitsunobu reaction;

DOI:10.1007/s12039-010-0066-z

upstream raw materials:

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

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

(1S,4S,5S)-5-((S)-1,2-dihydroxyethyl)cyclohex-2-ene-1,4-diol

(1S,4S,5R)-5-(hydroxymethyl)cyclohex-2-ene-1,4-diol

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