Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 131284-00-9
• Molecular Formula: C₃₄H₅₀O₁₆
• Molecular Weight: 714.761

Synonyms:

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-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: 52.0%

terpineol (98-55-5,2438-12-2) + 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosyl trichloracetamide (127243-74-7) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (131284-00-9,131348-57-7)

Guidance literature:

boron trifluoride diethyl etherate; In dichloromethane; benzene; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(90)80004-M

Reference yield:

2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranose (131283-99-3) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (131284-00-9,131348-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / K₂CO₃ / CH₂Cl₂ / 48 h / Ambient temperature

2: 52 percent / boron trifluoride etherate / benzene; CH₂Cl₂ / 2 h / Ambient temperature

With potassium carbonate; boron trifluoride diethyl etherate; In dichloromethane; benzene;

DOI:10.1016/0008-6215(90)80004-M

Reference yield:

Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside (5239-09-8,17073-40-4,29202-64-0,59684-89-8,62075-51-8,68398-82-3,70613-83-1,75828-89-6) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (131284-00-9,131348-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₃-CH₃OH / tetrahydrofuran / 0 °C

2: 72 percent / K₂CO₃ / CH₂Cl₂ / 48 h / Ambient temperature

3: 52 percent / boron trifluoride etherate / benzene; CH₂Cl₂ / 2 h / Ambient temperature

With methanol; ammonia; potassium carbonate; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/0008-6215(90)80004-M

upstream raw materials:

terpineol

2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosyl trichloracetamide

2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranose

Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside

Downstream raw materials:

(R,S)-α-terpinyl 6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

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