Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 210688-75-8
• Molecular Formula: C₁₈H₂₂O₇Se
• Molecular Weight: 429.328
• Mol file: 210688-75-8.mol

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-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: 94.0%

Benzeneselenol (645-96-5) + 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3) → Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester (210688-75-8)

Guidance literature:

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

DOI:10.1055/s-1998-3138

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester (210688-75-8) → (2R,4aR,6S,7R,8R,8aS)-8-((3aR,4S,6S,7R,7aS)-7-Hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (210688-83-8)

Guidance literature:

Multi-step reaction with 5 steps

1: MeONa, MeOH / Ambient temperature

2: CSA / CH₂Cl₂ / Ambient temperature

3: 1.) BuLi, 2.) DMAP / 1.) THF, -78 deg C to r.t., 2.) THF, r.t., 18 h

4: Bu₃SnH, AIBN / toluene / 17 h / 110 °C

5: nBu₄NF, H₂O / tetrahydrofuran / 1 h

With methanol; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium methylate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-1998-3138

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-6-methyl-2-phenylselanyl-tetrahydro-pyran-3-yl ester (210688-75-8) → (2R,4aR,6S,7R,8R,8aS)-7-((3aR,4S,6S,7R,7aS)-7-Hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (210688-77-0)

Guidance literature:

Multi-step reaction with 5 steps

1: MeONa, MeOH / Ambient temperature

2: CSA / CH₂Cl₂ / Ambient temperature

3: 1.) BuLi, 2.) DMAP / 1.) THF, -78 deg C to r.t., 2.) THF, r.t., 18 h

4: Bu₃SnH, AIBN / toluene / 17 h / 110 °C

5: nBu₄NF, H₂O / tetrahydrofuran / 1 h

With methanol; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; sodium methylate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-1998-3138

upstream raw materials:

Benzeneselenol

1,2,3,4-tetra-O-acetyl-β-L-fucopyranose

Downstream raw materials:

(3aR,4S,6R,7S,7aS)-2,2,4-Trimethyl-6-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

tert-Butyl-dimethyl-((3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-6-phenylselanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-silane

(2R,4aR,6S,7R,8R,8aS)-8-((3aR,4S,6S,7R,7aS)-7-Hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(3aR,4S,6S,7R,7aS)-6-((2S,3R,4S,5S,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-ylmethyl)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol