benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate

Base Information

• Chemical Name: benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate
• CAS No.: 316157-06-9
• Molecular Formula: C₅₀H₅₂O₁₂
• Molecular Weight: 844.956

Synonyms:benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate

Chemical Property of benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate

Chemical Property:

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Technology Process of benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate

There total 7 articles about benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate 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: 71.0%

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 (316157-05-8) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate (316157-06-9)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 6h;

DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate (316157-06-9)

Guidance literature:

Multi-step reaction with 6 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

6: 71 percent / MeOTf; 4 Angstroem mol. sieves / acetonitrile / 6 h / 20 °C

With dmap; sodium hydroxide; 4 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: acetal cleavage / 3: Alkylation / 4: Acylation / 5: oxidative cleavage / 6: Cyclization;

DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

benzyl bromide (100-39-0) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzyl-α-L-rhamnopyranoside 3,6'-malonate (316157-06-9)

Guidance literature:

Multi-step reaction with 4 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

4: 71 percent / MeOTf; 4 Angstroem mol. sieves / acetonitrile / 6 h / 20 °C

With dmap; sodium hydroxide; 4 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In dichloromethane; water; acetonitrile; 1: Alkylation / 2: Acylation / 3: oxidative cleavage / 4: Cyclization;

DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

upstream raw materials:

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

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

benzyl bromide

benzyl 4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside

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