Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 140654-70-2
• Molecular Formula: C₃₃H₄₆O₁₉S₂
• Molecular Weight: 810.849

Synonyms:

Chemical Property of Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester

There total 4 articles about Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-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: 45.0%

2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranose (92691-83-3) + methyl 2,3,6-tri-O-acetyl-4-S-<(1,4,5/6)- and (6/1,4,5)-4,5-epoxy-6-hydroxy-2-cyclohexen-1-yl>-4-thio-α-D-glucopyranoside (140654-69-9,140696-33-9) → Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester (140654-70-2,140696-34-0)

Guidance literature:

With water; In methanol; for 72h;

DOI:10.1016/0008-6215(92)84093-8

Reference yield:

methyl 2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-glucopyranoside (13264-04-5) → Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester (140654-70-2,140696-34-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / cysteamine, 1,4-dithioerythritol / hexamethylphosphoric acid triamide / 1 h / Ambient temperature

2: H₂O / methanol / 48 h

3: 73 percent / KOH, tetraethylammonium chloride / CH₂Cl₂ / 4 h

4: 45 percent / H₂O / methanol / 72 h

With potassium hydroxide; 1,4-dithio-erythritol; tetraethylammonium chloride; water; Cysteamine; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0008-6215(92)84093-8

Reference yield:

methyl 2,3,6-tri-O-acetyl-4-thio-α-D-glucopyranoside (140654-66-6) → Acetic acid (2S,3R,4R,5R,6R)-3-acetoxy-6-acetoxymethyl-5-[5,6-dihydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohex-2-enylsulfanyl]-2-methoxy-tetrahydro-pyran-4-yl ester (140654-70-2,140696-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂O / methanol / 48 h

2: 73 percent / KOH, tetraethylammonium chloride / CH₂Cl₂ / 4 h

3: 45 percent / H₂O / methanol / 72 h

With potassium hydroxide; tetraethylammonium chloride; water; In methanol; dichloromethane;

DOI:10.1016/0008-6215(92)84093-8

upstream raw materials:

2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranose

methyl 2,3,6-tri-O-acetyl-4-S-<(1,4,5/6)- and (6/1,4,5)-4,5-epoxy-6-hydroxy-2-cyclohexen-1-yl>-4-thio-α-D-glucopyranoside

methyl 2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-glucopyranoside

methyl 2,3,6-tri-O-acetyl-4-thio-α-D-glucopyranoside

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