4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 263358-72-1
• Molecular Formula: C₄₇H₆₀O₆S
• Molecular Weight: 753.056

Synonyms:4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of 4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester

There total 2 articles about 4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-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: 78.0%

C43H42O8 (263358-71-0) + 1-dodecylthiol (112-55-0) → 4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester (263358-72-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1246/cl.2000.122

Reference yield:

3,4,6-tri-O-benzyl-D-glucopyranose (20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1) → 4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester (263358-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / DMAP / pyridine / 0 - 20 °C

2: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

With dmap; boron trifluoride diethyl etherate; In pyridine; dichloromethane; 1: Acylation / 2: Alkylation;

DOI:10.1246/cl.2000.122

Reference yield: 90.0%

4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-dodecylsulfanyl-tetrahydro-pyran-3-yl ester (263358-72-1) → 4-Methyl-benzoic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:

With trifluorormethanesulfonic acid; tetrabutylammonium periodite; In acetonitrile; at 0 ℃;

DOI:10.1246/cl.2000.122

upstream raw materials:

C₄₃H₄₂O₈

1-dodecylthiol

3,4,6-tri-O-benzyl-D-glucopyranose

Downstream raw materials:

3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl phenylcarbonate

4-Methyl-benzoic acid (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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