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

Base Information

• Chemical Name: (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose
• CAS No.: 197916-17-9
• Molecular Formula: C₃₇H₄₄O₁₁
• Molecular Weight: 664.75
• Mol file: 197916-17-9.mol

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

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

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

There total 11 articles about (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose 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 (197916-17-9)

Guidance literature:

Multi-step reaction with 7 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

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;

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 (197916-17-9)

Guidance literature:

Multi-step reaction with 7 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

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;

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 (197916-17-9)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo971413u

upstream raw materials:

allyl α-L-rhamnopyranoside

benzyl bromide

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

2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside

Downstream raw materials:

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

Refernces