(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

Base Information

• Chemical Name: (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
• CAS No.: 1397285-59-4
• Molecular Formula: C₅₇H₆₀O₁₁
• Molecular Weight: 921.097

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 5 articles about (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 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: 50.0%

(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) → (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 (1397285-59-4)

Guidance literature:

With water; potassium carbonate; In methanol; at 20 ℃; for 1h;

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-{(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 (1397285-59-4)

Guidance literature:

Multi-step reaction with 5 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

5.1: potassium carbonate; water / methanol / 1 h / 20 °C

With ammonium cerium (IV) nitrate; diiodomethane; trimethylsilyl trifluoromethanesulfonate; water; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; 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-{(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 (1397285-59-4)

Guidance literature:

Multi-step reaction with 4 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

4: potassium carbonate; water / methanol / 1 h / 20 °C

With ammonium cerium (IV) nitrate; trimethylsilyl trifluoromethanesulfonate; water; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; 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

(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-{(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

Downstream raw materials:

(1S,3R,5S,6S,7S,8S)-1'-{2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl}-(1''→1')-{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-5'-yl)}-(5'→1)-6,7,8-tri-O-benzyl-5-O-methyl-4-oxaspiro[2.5]octane

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