methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside
• CAS No.: 615541-26-9
• Molecular Formula: C₃₀H₃₈O₁₀
• Molecular Weight: 558.626

Synonyms:methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property of methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property:

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Technology Process of methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

There total 8 articles about methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-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:

benzyl bromide (100-39-0) → methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside (615541-26-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-dibuthyltin oxide / benzene / 5 h / Heating

1.2: n-tetrabutylammonium iodide / benzene / 6 h / 50 °C

1.3: 70 percent / pyridine / 0.33 h / 0 - 20 °C

2.1: bromine / CH₂Cl₂ / 0 °C

2.2: 68 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / 50 °C

3.1: 85 percent / pyridine / various solvent(s) / 3 h / Heating

4.1: EtOH; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.25 h

4.2: 95 percent / NBS / 0.25 h / 0 °C

5.1: silver alumosilicate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

5.2: CH₂Cl₂ / 0.25 h

5.3: 80 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / 0 °C

With pyridine; ethanol; 3 A molecular sieve; 4 A molecular sieve; silver alumosilicate; bromine; di(n-butyl)tin oxide; In dichloromethane; benzene;

DOI:10.1002/ejoc.200300149

Reference yield:

benzoyl chloride (98-88-4) → methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside (615541-26-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / pyridine / 17 h / 20 °C

2.1: 85 percent / trifluoroacetic acid / methanol / 4.5 °C / Heating

3.1: n-dibuthyltin oxide / benzene / 5 h / Heating

3.2: n-tetrabutylammonium iodide / benzene / 6 h / 50 °C

3.3: 70 percent / pyridine / 0.33 h / 0 - 20 °C

4.1: bromine / CH₂Cl₂ / 0 °C

4.2: 68 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / 50 °C

5.1: 85 percent / pyridine / various solvent(s) / 3 h / Heating

6.1: EtOH; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.25 h

6.2: 95 percent / NBS / 0.25 h / 0 °C

7.1: silver alumosilicate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

7.2: CH₂Cl₂ / 0.25 h

7.3: 80 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / 0 °C

With pyridine; ethanol; 3 A molecular sieve; 4 A molecular sieve; silver alumosilicate; bromine; di(n-butyl)tin oxide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; benzene;

DOI:10.1002/ejoc.200300149

Reference yield:

methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (115678-10-9) → methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside (615541-26-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / pyridine / 17 h / 20 °C

2.1: 85 percent / trifluoroacetic acid / methanol / 4.5 °C / Heating

3.1: n-dibuthyltin oxide / benzene / 5 h / Heating

3.2: n-tetrabutylammonium iodide / benzene / 6 h / 50 °C

3.3: 70 percent / pyridine / 0.33 h / 0 - 20 °C

4.1: bromine / CH₂Cl₂ / 0 °C

4.2: 68 percent / 2,6-lutidine / CH₂Cl₂ / 19 h / 50 °C

5.1: 85 percent / pyridine / various solvent(s) / 3 h / Heating

6.1: EtOH; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.25 h

6.2: 95 percent / NBS / 0.25 h / 0 °C

7.1: silver alumosilicate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

7.2: CH₂Cl₂ / 0.25 h

7.3: 80 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / 0 °C

With pyridine; ethanol; 3 A molecular sieve; 4 A molecular sieve; silver alumosilicate; bromine; di(n-butyl)tin oxide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; benzene;

DOI:10.1002/ejoc.200300149

upstream raw materials:

benzyl bromide

benzoyl chloride

methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

methyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

methyl 2,3-O-isopropylidene-4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

methyl 2,3-O-isopropylidene-4-O-(2-O-acetyl-4-O-benzoyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside

methyl 2,3-O-isopropylidene-4-O-[2-O-acetyl-4-O-benzoyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Benzoic acid (2S,3S,4R,5R,6R)-5-acetoxy-6-((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

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