7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

Base Information

Chemical Name:7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose
CAS No.:302801-05-4
Molecular Formula:C₃₉H₄₈O₈
Molecular Weight:644.805
Hs Code.:

Synonyms:7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

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Chemical Property of 7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

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Technology Process of 7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

There total 12 articles about 7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose 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: 60.0%

: 302801-03-2
3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-xylo-hex-1-enyl (5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-D-xylo-heptofuranosid)uronate

: 74-95-3
1,1-dibromomethane

: 302801-05-4
7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

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:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 302801-05-4
7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: H₂SO₄

2: NaH

3: 75 percent / aq. HCl / H₂O

4: 62 percent / n-BuLi

5: 84 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

6: 60 percent / TiCl₄; Zn; TMEDA / PbCl₂ / tetrahydrofuran / 0.75 h / 60 °C

With hydrogenchloride; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; titanium tetrachloride; sodium hydride; dicyclohexyl-carbodiimide; zinc; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; 1: Methylation / 2: Alkylation / 3: Hydrolysis / 4: deprotonation / 4: Wittig reaction / 5: Esterification / 6: methylenation;
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 xylofuranoside

: 302801-05-4
7-O-(3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enyl)-5,6,8-trideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-octa-7-enofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: NaH

2: 75 percent / aq. HCl / H₂O

3: 62 percent / n-BuLi

4: 84 percent / 4-DMAP; DCC / CH₂Cl₂ / 20 °C

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

With hydrogenchloride; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; sodium hydride; dicyclohexyl-carbodiimide; zinc; lead(II) chloride; In tetrahydrofuran; dichloromethane; water; 1: Alkylation / 2: Hydrolysis / 3: deprotonation / 3: Wittig reaction / 4: Esterification / 5: methylenation;
DOI:10.1021/jo0005159