2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

Base Information

Chemical Name:2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside
CAS No.:1600528-74-2
Molecular Formula:C₅₁H₆₈O₈Si₂
Molecular Weight:865.267
Hs Code.:

Synonyms:2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

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Chemical Property of 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

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Technology Process of 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

There total 5 articles about 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-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: 63.0%

: 1600528-75-3
p-tolyl 3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-thio-β-D-glucopyranoside

: 246872-15-1
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethanol

: 1600528-74-2
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

Guidance literature:: p-tolyl 3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-thio-β-D-glucopyranoside; 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethanol; In dichloromethane; acetonitrile; at -60 - 20 ℃; for 0.333333h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; TMSOTf; In dichloromethane; acetonitrile; for 3h; Molecular sieve;
DOI:10.1039/c3ob42503g

Reference yield:

: p-tolyl 3-O-allyl-4,6-O-(2-naphthyl)methylene-1-thio-β-D-glucopyranoside

: 1600528-74-2
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Molecular sieve

3.1: dichloromethane; acetonitrile / 0.33 h / -60 - 20 °C / Molecular sieve; Inert atmosphere

3.2: 3 h / Molecular sieve

With triethylsilane; sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/c3ob42503g

Reference yield:

: p-tolyl3-O-allyl-2-O-(2-naphthyl)methyl-4,6-O-(2-naphthyl)methylene-1-thio-β-D-glucopyranoside

: 1600528-74-2
2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-ethyl-3-O-allyl-2,6-di-O-(2-naphthyl)methyl-1-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Molecular sieve

2.1: dichloromethane; acetonitrile / 0.33 h / -60 - 20 °C / Molecular sieve; Inert atmosphere

2.2: 3 h / Molecular sieve

With triethylsilane; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1039/c3ob42503g