2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

Base Information

Chemical Name:2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose
CAS No.:250740-76-2
Molecular Formula:C₆₄H₈₂O₂₀Si₂
Molecular Weight:1227.51
Hs Code.:

Synonyms:2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

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Chemical Property of 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

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Technology Process of 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

There total 24 articles about 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose 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: 61.0%

: 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 4,6-O-benzylidene-2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

: 250740-76-2
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

Guidance literature:: With toluene-4-sulfonic acid; ethylene glycol; In dichloromethane; for 48h;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

: 25379-88-8
2-(3,4-dihydroxyphenyl)acetic acid methyl ester

: 250740-76-2
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 2 h

2: 91 percent / LiAlH₄ / diethyl ether / 0.25 h

3: 58 percent / BF₃*OEt₂ / CH₂Cl₂

4: 98 percent / NaOMe / methanol / 3.5 h

5: 90 percent / pyridine / CH₂Cl₂ / 2 h

6: 61 percent / ethylene glycol; p-toluenesulfonic acid / CH₂Cl₂ / 48 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; ethylene glycol; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Etherification / 4: deacylation / 5: Acylation / 6: Hydrolysis;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

: 246872-14-0
methyl [3,4-bis(tert-butyldimethylsilyloxy)phenyl]acetate

: 250740-76-2
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / LiAlH₄ / diethyl ether / 0.25 h

2: 58 percent / BF₃*OEt₂ / CH₂Cl₂

3: 98 percent / NaOMe / methanol / 3.5 h

4: 90 percent / pyridine / CH₂Cl₂ / 2 h

5: 61 percent / ethylene glycol; p-toluenesulfonic acid / CH₂Cl₂ / 48 h

With pyridine; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; ethylene glycol; In methanol; diethyl ether; dichloromethane; 1: Reduction / 2: Etherification / 3: deacylation / 4: Acylation / 5: Hydrolysis;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k