11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester

Base Information

• Chemical Name: 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester
• CAS No.: 929296-57-1
• Molecular Formula: C₄₃H₆₈O₁₃
• Molecular Weight: 793.005

Synonyms:11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester

Chemical Property of 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester

Chemical Property:

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Technology Process of 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester

There total 12 articles about 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl 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: 96.0%

1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-O-isopropylidene-α-L-rhamnopyranoside (115655-84-0) + 2,3-di-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate (294677-66-0) → 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester (929296-57-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1055/s-2006-956493

Reference yield:

(S)-1-benzyloxy-11-hexadecanol (929296-51-5) → 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester (929296-57-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / pyridine / 20 °C

2: 85 percent / H₂ / Pd/C / ethanol / 60 °C

3: 67 percent / Jones reagent / acetone / 20 °C

4: 85 percent / boron trifluoride-diethyl ether / 40 °C

5: 66 percent / boron trifluoride-diethyl ether / CH₂Cl₂ / -78 - 20 °C

6: NaOMe / methanol / -20 °C

7: p-TsOH / dimethylformamide / 20 °C

8: 96 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -78 - 20 °C

With jones reagent; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; sodium methylate; toluene-4-sulfonic acid; palladium on activated charcoal; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 3: Jones oxidation;

DOI:10.1055/s-2006-956493

Reference yield:

acetic acid 11-benzyloxy-1-pentyl-undecyl ester (929296-52-6) → 11-[7-(3,4-diacetoxy-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy]-hexadecanoic acid methyl ester (929296-57-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / H₂ / Pd/C / ethanol / 60 °C

2: 67 percent / Jones reagent / acetone / 20 °C

3: 85 percent / boron trifluoride-diethyl ether / 40 °C

4: 66 percent / boron trifluoride-diethyl ether / CH₂Cl₂ / -78 - 20 °C

5: NaOMe / methanol / -20 °C

6: p-TsOH / dimethylformamide / 20 °C

7: 96 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -78 - 20 °C

With jones reagent; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; sodium methylate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; 2: Jones oxidation;

DOI:10.1055/s-2006-956493

upstream raw materials:

1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-O-isopropylidene-α-L-rhamnopyranoside

2,3-di-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

acetic acid 11-hydroxy-1-pentyl-undecyl ester

(S)-1-benzyloxy-11-hexadecanol

Downstream raw materials:

C₃₈H₆₀O₁₀

1-(hydroxycarbonyl)pentadec-10(S)-yl 4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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