(2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

Base Information

Chemical Name:(2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol
CAS No.:242808-60-2
Molecular Formula:C₁₅H₂₂O₄
Molecular Weight:266.337
Hs Code.:

Synonyms:(2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

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Chemical Property of (2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

Chemical Property:

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Technology Process of (2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

There total 1 articles about (2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol 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: 85.0%

: 85531-70-0
[3-(2-Benzyloxy-ethyl)-oxiranyl]-methanol

: 107-18-6
allyl alcohol

: 242808-60-2
(2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

Guidance literature:: With titanium(IV) isopropylate; In toluene; for 5h; Heating;
DOI:10.1055/s-1999-2784

Reference yield:

: 242808-60-2
(2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

: 242808-91-9
(2R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-hexahydro-1,5-dioxa-benzocyclohepten-3-one

Guidance literature:: Multi-step reaction with 13 steps

1: DMAP, pyridine / CH₂Cl₂ / 14 h / 20 - 25 °C

2: K₂CO₃ / methanol / 6 h / 20 - 23 °C

3: 1.) CuCN / 1.) THF, -78 to -40 deg C, 1 h, 2.) THF, -40 deg C, 1.3 h

4: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 2 h / Heating

5: H₂ / RhCl(PPh₃)3 / benzene / 9 h / 21 °C

6: imidazole / dimethylformamide / 3 h / 24 °C

7: H₂ / 10 percent Pd/C / methanol / 2 h / 21 °C

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 to 0 deg C

9: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 20 min

10: TBAF / tetrahydrofuran / 25 °C

11: 44 percent / TsOH*H₂O / methanol / 20 - 25 °C

12: 70 percent / Et₃SiH, SnCl₄ / -78 - 0 °C

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 to 0 deg C

With pyridine; 1H-imidazole; triethylsilane; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tin(IV) chloride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Grubbs catalyst first generation; RhCl(PPh₃)3; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1055/s-1999-2784

Reference yield:

: 242808-60-2
(2S,3R)-3-Allyloxy-5-benzyloxy-pentane-1,2-diol

: (2S,3R,4aR,9aS)-2-((2S,3R)-3-Benzyloxy-oxepan-2-ylmethyl)-octahydro-1,5-dioxa-benzocyclohepten-3-ol

Guidance literature:: Multi-step reaction with 12 steps

1: DMAP, pyridine / CH₂Cl₂ / 14 h / 20 - 25 °C

2: K₂CO₃ / methanol / 6 h / 20 - 23 °C

3: 1.) CuCN / 1.) THF, -78 to -40 deg C, 1 h, 2.) THF, -40 deg C, 1.3 h

4: (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 2 h / Heating

5: H₂ / RhCl(PPh₃)3 / benzene / 9 h / 21 °C

6: imidazole / dimethylformamide / 3 h / 24 °C

7: H₂ / 10 percent Pd/C / methanol / 2 h / 21 °C

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 to 0 deg C

9: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 20 min

10: TBAF / tetrahydrofuran / 25 °C

11: 44 percent / TsOH*H₂O / methanol / 20 - 25 °C

12: 9 percent / Et₃SiH, SnCl₄ / -78 - 0 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tin(IV) chloride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Grubbs catalyst first generation; RhCl(PPh₃)3; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1055/s-1999-2784