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

Base Information

• Chemical Name: (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate
• CAS No.: 197916-18-0
• Molecular Formula: C₃₉H₄₄Cl₃NO₁₁
• Molecular Weight: 809.137
• Mol file: 197916-18-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate 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:

allyl α-L-rhamnopyranoside (64650-81-3) → (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate (197916-18-0)

Guidance literature:

Multi-step reaction with 8 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

6: n-BuLi / (Ph₃P)3RhCl / tetrahydrofuran; hexane / 0.25 h / Heating

7: 334 mg / HgCl₂; HgO / H₂O; acetone / 2 h

8: Cs₂CO₃ / CH₂Cl₂ / 11 h

With hydrogenchloride; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; caesium carbonate; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Isomerization / 3: Hydrolysis / 4: Addition / 5: glycosylation / 6: Isomerization / 7: Hydrolysis / 8: Addition;

DOI:10.1021/jo971413u

Reference yield:

benzyl bromide (100-39-0) → (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate (197916-18-0)

Guidance literature:

Multi-step reaction with 8 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

6: n-BuLi / (Ph₃P)3RhCl / tetrahydrofuran; hexane / 0.25 h / Heating

7: 334 mg / HgCl₂; HgO / H₂O; acetone / 2 h

8: Cs₂CO₃ / CH₂Cl₂ / 11 h

With hydrogenchloride; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; caesium carbonate; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Isomerization / 3: Hydrolysis / 4: Addition / 5: glycosylation / 6: Isomerization / 7: Hydrolysis / 8: Addition;

DOI:10.1021/jo971413u

Reference yield:

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate (83866-10-8) → (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 1-trichloroacetimidate (197916-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h

2: n-BuLi / (Ph₃P)3RhCl / tetrahydrofuran; hexane / 0.25 h / Heating

3: 334 mg / HgCl₂; HgO / H₂O; acetone / 2 h

4: Cs₂CO₃ / CH₂Cl₂ / 11 h

With n-butyllithium; boron trifluoride diethyl etherate; caesium carbonate; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; water; acetone; 1: glycosylation / 2: Isomerization / 3: Hydrolysis / 4: Addition;

DOI:10.1021/jo971413u

upstream raw materials:

trichloroacetonitrile

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

allyl α-L-rhamnopyranoside

benzyl bromide

Refernces