(1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan

Base Information

• Chemical Name: (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan
• CAS No.: 1397285-55-0
• Molecular Formula: C₃₅H₄₀O₇
• Molecular Weight: 572.698

Synonyms:(1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan

Chemical Property of (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan

There total 4 articles about (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan 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:

n-Pent-4-enyl alcohol (821-09-0) + (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-(2',2',2'-trichloro-1-iminoethoxy)-4-oxaspiro[2.5]octane (1397285-45-8) → (1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan (1397285-56-1) + (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan (1397285-55-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; at 0 ℃; for 3h; Overall yield = 76 %; Overall yield = 23 mg; Inert atmosphere;

DOI:10.1021/ol3024133 DOI:10.1021/ol3024133

Reference yield:

p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside → (1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan (1397285-56-1) + (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan (1397285-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diiodomethane / toluene; 1,2-dichloro-ethane / 0.25 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 48 h / 50 °C / Molecular sieve; Inert atmosphere

2.1: ammonium cerium (IV) nitrate / acetonitrile; toluene; aq. phosphate buffer / 1 h / 20 °C / pH 7 / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; toluene / 0 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane; toluene / 3 h / 0 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; diiodomethane; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In aq. phosphate buffer; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1021/ol3024133 DOI:10.1021/ol3024133

Reference yield:

(1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-pmethoxyphenyl-4-oxaspiro[2.5]octane (1397285-43-6) → (1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan (1397285-56-1) + (1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-pent-4'-enyl-4-oxaspiro[2.5]octan (1397285-55-0)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium cerium (IV) nitrate / acetonitrile; toluene; aq. phosphate buffer / 1 h / 20 °C / pH 7 / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; toluene / 0 °C / Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane; toluene / 3 h / 0 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In aq. phosphate buffer; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ol3024133 DOI:10.1021/ol3024133

upstream raw materials:

(1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-pmethoxyphenyl-4-oxaspiro[2.5]octane

n-Pent-4-enyl alcohol

(1S,3R,5R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-(2',2',2'-trichloro-1-iminoethoxy)-4-oxaspiro[2.5]octane

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