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

Base Information

• Chemical Name: 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
• CAS No.: 615541-33-8
• Molecular Formula: C₃₄H₄₆O₁₈
• Molecular Weight: 742.728

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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:

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 (615541-31-6) → 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 (615541-33-8)

Guidance literature:

With trifluoroacetic acid; In acetic acid; at 35 ℃; for 3.5h;

DOI:10.1002/ejoc.200300149

Reference yield:

benzoyl chloride (98-88-4) → 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 (615541-33-8)

Guidance literature:

Multi-step reaction with 11 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

8.1: 92 percent / pyridine / 12 h / 20 °C

9.1: 99 percent / H₂ / Pd(OH)2/C/20percent / ethyl acetate / 17 h / 20 °C

10.1: 82 percent / AgOTf; molecular sieves 4 Angstroem; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.67 h / -45 - -5 °C

11.1: trifluoroacetic acid / acetic acid / 3.5 h / 35 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; ethanol; 3 A molecular sieve; 4 A molecular sieve; silver alumosilicate; hydrogen; bromine; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; trifluoroacetic acid; Pd(OH)2/C/20percent; In pyridine; methanol; dichloromethane; acetic acid; ethyl acetate; benzene;

DOI:10.1002/ejoc.200300149

Reference yield:

methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (115678-10-9) → 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 (615541-33-8)

Guidance literature:

Multi-step reaction with 11 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

8.1: 92 percent / pyridine / 12 h / 20 °C

9.1: 99 percent / H₂ / Pd(OH)2/C/20percent / ethyl acetate / 17 h / 20 °C

10.1: 82 percent / AgOTf; molecular sieves 4 Angstroem; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.67 h / -45 - -5 °C

11.1: trifluoroacetic acid / acetic acid / 3.5 h / 35 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; ethanol; 3 A molecular sieve; 4 A molecular sieve; silver alumosilicate; hydrogen; bromine; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; trifluoroacetic acid; Pd(OH)2/C/20percent; In pyridine; methanol; dichloromethane; acetic acid; ethyl acetate; benzene;

DOI:10.1002/ejoc.200300149

upstream raw materials:

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

benzoyl chloride

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

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

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