3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate
• CAS No.: 302800-88-0
• Molecular Formula: C₄₁H₅₀O₁₀
• Molecular Weight: 702.842
• Mol file: 302800-88-0.mol

Synonyms:3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate

Chemical Property of 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate

There total 9 articles about 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate 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: 90.0%

6,7-Dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octapyranuronic acid (174501-67-8) + 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enitol (302800-64-2) → 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate (302800-88-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0005159

Reference yield:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) → 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate (302800-88-0)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 4 h / 20 °C

2: 95 percent / H₂ / Lindlar catalyst / ethyl acetate / 20 °C / 1810.07 Torr

3: 98 percent / LiOH / tetrahydrofuran; H₂O / 20 °C / Saponification

4: 90 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; hydrogen; dicyclohexyl-carbodiimide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; ethyl acetate; benzene; 1: Wittig reaction / 2: Catalytic hydrogenation / 3: Hydrolysis / 4: Esterification;

DOI:10.1021/jo0005159

Reference yield:

ethyl 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-6-eno-octopyranuronate (71553-90-7) → 3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl (6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranosid)uronate (302800-88-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂ / Lindlar catalyst / ethyl acetate / 20 °C / 1810.07 Torr

2: 98 percent / LiOH / tetrahydrofuran; H₂O / 20 °C / Saponification

3: 90 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; hydrogen; dicyclohexyl-carbodiimide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 1: Catalytic hydrogenation / 2: Hydrolysis / 3: Esterification;

DOI:10.1021/jo0005159

upstream raw materials:

6,7-Dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octapyranuronic acid

3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enitol

Methyl α-lyxofuranoside

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

Downstream raw materials:

methyl 8-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-lyxo-hex-1-enyl)-6,7,9-trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-nona-8-enopyranose