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

Base Information

Chemical Name:{(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'→6)-methyl 2,3,4-tri-O-benzyl-a-D-mannoside
CAS No.:1397285-50-5
Molecular Formula:C₅₈H₆₂O₁₂
Molecular Weight:951.123
Hs Code.:

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

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

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

There total 4 articles about {(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'→6)-methyl 2,3,4-tri-O-benzyl-a-D-mannoside 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:

: 34212-64-1,641635-63-4
methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

: 1397285-45-8
(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

: 1397285-49-2
{(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

: 1397285-50-5
{(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'→6)-methyl 2,3,4-tri-O-benzyl-a-D-mannoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; at 0 ℃; for 3h; Overall yield = 70 %; Overall yield = 41 mg; Inert atmosphere;
DOI:10.1021/ol3024133 DOI:10.1021/ol3024133

Reference yield:

: 1397285-43-6
(1S,3R,5S,6S,7S,8S)-1-O-acetyl-6,7,8-tri-O-benzyl-5-O-pmethoxyphenyl-4-oxaspiro[2.5]octane

: 1397285-49-2
{(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

: 1397285-50-5
{(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'→6)-methyl 2,3,4-tri-O-benzyl-a-D-mannoside

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

Reference yield:

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

: 1397285-49-2
{(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

: 1397285-50-5
{(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'→6)-methyl 2,3,4-tri-O-benzyl-a-D-mannoside

Guidance literature:: Multi-step reaction with 2 steps

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

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

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene;
DOI:10.1021/ol3024133 DOI:10.1021/ol3024133