ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside
CAS No.:197853-53-5
Molecular Formula:C₄₅H₆₀O₁₀S
Molecular Weight:793.031
Hs Code.:

Synonyms:ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

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Chemical Property of ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

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Technology Process of ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

There total 7 articles about ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside 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: 98.0%

: 128962-63-0,116391-11-8
ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside

: 197853-35-3
ethyl 2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

: 197853-53-5
ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

Guidance literature:: With iodonium(di-γ-collidine) perchlorate; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1002/anie.199723441

Reference yield:

: 127753-94-0
ethyl 1-thio-α-L-rhamnopyranoside

: 197853-53-5
ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₂SnO; 4 Angstroem molecular sieves / toluene / 1 h / Heating

1.2: 79 percent / CsF; Bu₄NI / dimethylformamide / 33 h / 20 °C

2.1: 69.7 percent / DMAP; pyridine / 27 h / 20 °C

3.1: 97.5 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 0.42 h / 20 °C

4.1: 98 percent / 4 Angstroem MS; iodium di-sym-collidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 0.5 h / 20 °C

With pyridine; dmap; ammonium cerium(IV) nitrate; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; 4 Angstroem MS; di(n-butyl)tin oxide; In diethyl ether; water; 1,2-dichloro-ethane; toluene; acetonitrile; 1.1: stannylation / 1.2: Alkylation / 2.1: Acylation / 3.1: Oxidation / 4.1: glycosylation;
DOI:10.1021/jo9711450

Reference yield:

: 179337-13-4
ethyl 3-O-(p-methoxybenzyl)-1-thio-α-L-rhamnopyranoside

: 197853-53-5
ethyl O-[2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl]-(1->3)-2,4-di-O-[2(S)-methylbutyryl]-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 69.7 percent / DMAP; pyridine / 27 h / 20 °C

2: 97.5 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 0.42 h / 20 °C

3: 98 percent / 4 Angstroem MS; iodium di-sym-collidine perchlorate / diethyl ether; 1,2-dichloro-ethane / 0.5 h / 20 °C

With pyridine; dmap; ammonium cerium(IV) nitrate; iodonium(di-γ-collidine) perchlorate; 4 Angstroem MS; In diethyl ether; water; 1,2-dichloro-ethane; acetonitrile; 1: Acylation / 2: Oxidation / 3: glycosylation;
DOI:10.1021/jo9711450