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

Base Information

• Chemical Name: (1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-pmethoxyphenyl-4-oxaspiro[2.5]octane
• CAS No.: 1397285-43-6
• Molecular Formula: C₃₇H₃₈O₈
• Molecular Weight: 610.704
• Mol file: 1397285-43-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-pmethoxyphenyl-4-oxaspiro[2.5]octane 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: 27.0%

p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside → (1R,3S,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-p-methoxyphenyl-4-oxaspiro[2.5]octane (1397285-42-5) + (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)

Guidance literature:

p-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannohex-5-enopyranoside; With diiodomethane; In 1,2-dichloro-ethane; toluene; at 20 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With diethylzinc; In hexane; 1,2-dichloro-ethane; toluene; at 50 ℃; for 48h; Molecular sieve; Inert atmosphere;

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,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-4-oxaspiro[2.5]octan-5-ol

Guidance literature:

With ammonium cerium (IV) nitrate; In aq. phosphate buffer; toluene; acetonitrile; at 20 ℃; for 1h; pH=7; Inert atmosphere;

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-{(1'S,3'R,5'S,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan (1397285-47-0)

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

Downstream raw materials:

(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

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

(1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'S,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan

(1S,3R,5S,6S,7S,8S)-1-O-{(1'S,3'R,5'R,6'S,7'S,8'S)-1'-O-acetyl-6',7',8'-tri-O-benzyl-4'-oxaspiro[2.5]octan-5'-yl}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octan