(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

Base Information

• Chemical Name: (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
• CAS No.: 1397285-45-8
• Molecular Formula: C₃₂H₃₂Cl₃NO₇
• Molecular Weight: 648.968

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 3 articles about (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 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:

(1S,3R,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-4-oxaspiro[2.5]octan-5-ol + trichloroacetonitrile (545-06-2) → (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-(2',2',2'-trichloro-1-iminoethoxy)-4-oxaspiro[2.5]octane (1397285-46-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; at 0 ℃; Overall yield = 76 %; Overall yield = 41 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,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-(2',2',2'-trichloro-1-iminoethoxy)-4-oxaspiro[2.5]octane (1397285-46-9)

Guidance literature:

Multi-step reaction with 3 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

With ammonium cerium (IV) nitrate; diiodomethane; 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,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-(2',2',2'-trichloro-1-iminoethoxy)-4-oxaspiro[2.5]octane (1397285-46-9)

Guidance literature:

Multi-step reaction with 2 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

With ammonium cerium (IV) nitrate; 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

trichloroacetonitrile

Downstream raw materials:

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

{(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'→6)-methyl 2,3,4-tri-O-benzyl-a-D-mannoside

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