ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside
CAS No.:316157-05-8
Molecular Formula:C₅₂H₅₈O₁₂S
Molecular Weight:907.091
Hs Code.:

Synonyms:ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

There total 6 articles about ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside 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: 84.0%

: 316157-04-7
ethyl 2,3,4-tri-O-benzyl-6-O-{3-[benzyl 2-O-benzyl-4-O-(4-methoxybenzyl)-α-L-rhamnopyranosid-3-O-yl]-1,3-dioxopropyl}-1-thio-α-D-mannopyranoside

: 316157-05-8
ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h;
DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

: 53270-14-7
benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 316157-05-8
ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / NaH / dimethylformamide / 3 h / 0 - 20 °C

2: 89 percent / aq. AcOH / H₂O / 3 h / 60 °C

3: 77 percent / Bu₄N(HSO₄); aq. NaOH / CH₂Cl₂; H₂O / 6 h / -5 °C

4: 69 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

5: 84 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With dmap; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; 1: Acylation / 2: acetal cleavage / 3: Alkylation / 4: Acylation / 5: oxidative cleavage;
DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

: 100-39-0
benzyl bromide

: 316157-05-8
ethyl 2,3,4-tri-O-benzyl-6-O-[3-(benzyl 2-O-benzyl-α-L-rhamnopyranosid-3-O-yl)-1,3-dioxopropyl]-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / Bu₄N(HSO₄); aq. NaOH / CH₂Cl₂; H₂O / 6 h / -5 °C

2: 69 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 84 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With dmap; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; 1: Alkylation / 2: Acylation / 3: oxidative cleavage;
DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K