1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

Base Information

Chemical Name:1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside
CAS No.:935554-44-2
Molecular Formula:C₅₇H₆₆O₈
Molecular Weight:879.146
Hs Code.:

Synonyms:1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

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Chemical Property of 1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

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Technology Process of 1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

There total 4 articles about 1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside 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: 79.0%

: 935554-41-9
ethyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-1-thio-β-D-glucopyranoside

: 768-95-6
1-adamanthanol

: 935554-44-2
1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; In dichloromethane; at -40 ℃; for 0.25h;
DOI:10.1021/ol070449y

Reference yield:

: 40662-14-4
4,4,5,7-tetramethyl-3,4-dihydrocoumarin

: 935554-44-2
1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: KOH / methanol / 3 h / 20 °C

1.2: NaH / acetonitrile; various solvent(s) / 0 - 20 °C

1.3: 64 percent / water / acetonitrile; various solvent(s) / 5 h / 0 °C

2.1: 1,1'-carbonyldiimidazole / acetonitrile / 2 h / 60 °C

2.2: 87 percent / DBU / acetonitrile / 3 h / 60 °C

3.1: 79 percent / trifluoromethanesulfonic acid; NIS; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.25 h / -40 °C

With potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 1,1'-carbonyldiimidazole; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol070449y

Reference yield:

: 100-39-0
benzyl bromide

: 935554-44-2
1-adamantanyl 3,4,6-tri-O-benzyl-2-O-[3'-(2''-benzyloxy-4'',6''-dimethylphenyl)-3',3'-dimethylpropanoyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: KOH / methanol / 3 h / 20 °C

1.2: NaH / acetonitrile; various solvent(s) / 0 - 20 °C

1.3: 64 percent / water / acetonitrile; various solvent(s) / 5 h / 0 °C

2.1: 1,1'-carbonyldiimidazole / acetonitrile / 2 h / 60 °C

2.2: 87 percent / DBU / acetonitrile / 3 h / 60 °C

3.1: 79 percent / trifluoromethanesulfonic acid; NIS; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.25 h / -40 °C

With potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 1,1'-carbonyldiimidazole; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol070449y