3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose

Base Information

Chemical Name:3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose
CAS No.:162179-07-9
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

Synonyms:

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Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose

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Technology Process of 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose

There total 10 articles about 3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose 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:

: dithiocarbonic acid S-{1-[benzyloxy-(6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methyl]-allyl} ester S-methyl ester

: 162179-07-9
3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose

Guidance literature:: dithiocarbonic acid S-{1-[benzyloxy-(6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methyl]-allyl} ester S-methyl ester; With tri-n-butyl-tin hydride; In toluene; for 0.5h; Heating;

With zinc chloride diethyl ether; In dichloromethane; at 20 ℃; for 0.333333h;
DOI:10.1016/S0957-4166(00)00135-X

Reference yield:

: 28713-39-5
3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 162179-07-9
3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

2.1: benzene / 16 h / 20 °C

3.1: DIBAL-H / hexane; CH₂Cl₂ / 2 h / -78 °C

4.1: sodium hydride; imidazole / tetrahydrofuran / 1 h / 20 °C

4.2: tetrahydrofuran / 0.5 h / 20 °C

5.1: tetrahydrofuran / 2 h / 20 °C

6.1: toluene / 3 h / Heating

7.1: tri-n-butyltin hydride / toluene / 0.5 h / Heating

7.2: ZnCl₂ etherate / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; oxalyl dichloride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene; 1.1: Swern oxidation / 2.1: Wittig reaction / 3.1: Reduction / 4.1: Metallation / 4.2: Addition / 5.1: Methylation / 6.1: Rearrangement / 7.1: Addition / 7.2: Elimination;
DOI:10.1016/S0957-4166(00)00135-X

Reference yield:

: 115243-95-3
(S)-Benzyloxy-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde

: 162179-07-9
3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-α-D-xylo-oct-5(E),7-dieno-1,4-furanose

Guidance literature:: Multi-step reaction with 6 steps

1.1: benzene / 16 h / 20 °C

2.1: DIBAL-H / hexane; CH₂Cl₂ / 2 h / -78 °C

3.1: sodium hydride; imidazole / tetrahydrofuran / 1 h / 20 °C

3.2: tetrahydrofuran / 0.5 h / 20 °C

4.1: tetrahydrofuran / 2 h / 20 °C

5.1: toluene / 3 h / Heating

6.1: tri-n-butyltin hydride / toluene / 0.5 h / Heating

6.2: ZnCl₂ etherate / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene; 1.1: Wittig reaction / 2.1: Reduction / 3.1: Metallation / 3.2: Addition / 4.1: Methylation / 5.1: Rearrangement / 6.1: Addition / 6.2: Elimination;
DOI:10.1016/S0957-4166(00)00135-X