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

Base Information

Chemical Name: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
CAS No.:302800-90-4
Molecular Formula:C₄₂H₅₂O₉
Molecular Weight:700.869
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 68.0%

: 302800-88-0
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

: 74-95-3
1,1-dibromomethane

: 302800-90-4
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

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride; In tetrahydrofuran; at 60 ℃; for 0.75h;
DOI:10.1021/jo0005159

Reference yield:

: 1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7
Methyl α-lyxofuranoside

: 302800-90-4
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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4.08 g / NaH / dimethylformamide

2.1: 72 percent / glac. acetic acid; H₂SO₄ / H₂O / 0.58 h / 100 °C

3.1: n-BuLi / tetrahydrofuran

3.2: 50 percent / tetrahydrofuran

4.1: 90 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

5.1: 68 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 0.75 h / 60 °C

With dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; titanium tetrachloride; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; zinc; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: deprotonation / 3.2: Wittig reaction / 4.1: Esterification / 5.1: methylenation;
DOI:10.1021/jo0005159

Reference yield:

: 4933-77-1
(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

: 302800-90-4
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

Guidance literature:: Multi-step reaction with 5 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

5: 68 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 0.75 h / 60 °C

With dmap; lithium hydroxide; N,N,N,N,-tetramethylethylenediamine; hydrogen; titanium tetrachloride; dicyclohexyl-carbodiimide; zinc; Lindlar's catalyst; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; ethyl acetate; benzene; 1: Wittig reaction / 2: Catalytic hydrogenation / 3: Hydrolysis / 4: Esterification / 5: methylenation;
DOI:10.1021/jo0005159