allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

Base Information

Chemical Name:allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside
CAS No.:197916-09-9
Molecular Formula:C₄₀H₄₈O₁₁
Molecular Weight:704.815
Hs Code.:

Synonyms:allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

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Chemical Property of allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

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Technology Process of allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

There total 8 articles about allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-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: 93.0%

: 83866-10-8
(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

: 197916-08-8
allyl 2,4-di-O-acetyl-α-L-rhamnopyranoside

: 197916-09-9
allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; for 2h;
DOI:10.1021/jo971413u

Reference yield:

: 64650-81-3
allyl α-L-rhamnopyranoside

: 197916-09-9
allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / NaH; Bu₄NI / dimethylformamide

2: t-BuOK / dimethylsulfoxide / 0.25 h / 100 °C

3: 825 mg / aq. HCl / acetone / 0.5 h / Heating

4: Cs₂CO₃ / CH₂Cl₂ / 3.5 h

5: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

With hydrogenchloride; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; caesium carbonate; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Isomerization / 3: Hydrolysis / 4: Addition / 5: glycosylation;
DOI:10.1021/jo971413u

Reference yield:

: 100-39-0
benzyl bromide

: 197916-09-9
allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / NaH; Bu₄NI / dimethylformamide

2: t-BuOK / dimethylsulfoxide / 0.25 h / 100 °C

3: 825 mg / aq. HCl / acetone / 0.5 h / Heating

4: Cs₂CO₃ / CH₂Cl₂ / 3.5 h

5: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

With hydrogenchloride; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; caesium carbonate; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Isomerization / 3: Hydrolysis / 4: Addition / 5: glycosylation;
DOI:10.1021/jo971413u