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

Base Information

• Chemical Name: (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α/β-L-rhamnopyranose trichloroacetimidate
• CAS No.: 1091625-15-8
• Molecular Formula: C₄₂H₄₈Cl₃NO₁₂
• Molecular Weight: 865.202

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α/β-L-rhamnopyranose 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: 92.0%

(3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α/β-L-rhamnopyranose + trichloroacetonitrile (545-06-2) → (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α/β-L-rhamnopyranose trichloroacetimidate (1091625-15-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane; at -5 ℃; for 0.25h; Inert atmosphere;

Reference yield:

L-rhamnose (73-34-7) → (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α/β-L-rhamnopyranose trichloroacetimidate (1091625-15-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetyl chloride / 0.25 h / 0 °C

1.2: 40 - 70 °C

2.1: toluene-4-sulfonic acid / acetone / 2 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -5 - 20 °C / Inert atmosphere

3.2: 4 h / -5 - 20 °C / Inert atmosphere

4.1: acetic acid / water / 3 h / 60 °C

5.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 20 °C

5.2: 1 h / 20 °C / Cooling with ice

6.1: trimethylsilyl trifluoromethanesulfonate / toluene / 1.5 h / -78 °C / Molecular sieve; Inert atmosphere

7.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / Inert atmosphere

7.2: Inert atmosphere

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dichloro-ethane / 0.25 h / -5 °C / Inert atmosphere

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In tetrahydrofuran; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;

Reference yield:

3,4-di-O-benzyl-2-O-levulinoyl-L-rhamnopyranose trichloroacetimidate (1091625-16-9) → (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-benzyl-α/β-L-rhamnopyranose trichloroacetimidate (1091625-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trimethylsilyl trifluoromethanesulfonate / toluene / 1.5 h / -78 °C / Molecular sieve; Inert atmosphere

2.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / Inert atmosphere

2.2: Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dichloro-ethane / 0.25 h / -5 °C / Inert atmosphere

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,2-dichloro-ethane; toluene;

upstream raw materials:

trichloroacetonitrile

3,4-di-O-benzyl-2-O-levulinoyl-L-rhamnopyranose trichloroacetimidate

L-rhamnose

benzyl bromide

Downstream raw materials:

allyl (2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-3O-trimethylsilyl-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

allyl (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

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