(4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether

Base Information

Chemical Name:(4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether
CAS No.:113195-16-7
Molecular Formula:C₂₂H₂₈O₄
Molecular Weight:356.462
Hs Code.:

Synonyms:

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Chemical Property of (4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether

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Technology Process of (4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether

There total 14 articles about (4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether 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: 80.0%

: 100-39-0
benzyl bromide

: 113195-12-3,113195-13-4
(4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol

: 113195-16-7,113195-17-8
(4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; paraffin; for 1h; Heating;
DOI:10.1016/S0040-4020(01)89929-4

Reference yield:

: 1830-54-2
3-oxopentanedioic acid dimethyl ester

: 113195-16-7,113195-17-8
(4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether

Guidance literature:: Multi-step reaction with 14 steps

1: NaBH₄ / methanol

2: p-TsOH*H₂O / diethyl ether

3: LiAlH₄ / diethyl ether

4: p-TsOH*H₂O / methanol

5: 98.3 g / p-TsOH*H₂O / acetone

6: 97 percent / pyridinium chlorochromate, MS (3 Angstroem) / CH₂Cl₂

7: 64 percent / p-TsOH*H₂O / CH₂Cl₂ / Heating

8: 72 percent / pyridinium dichromate, MS (3 Angstroem) / CH₂Cl₂

9: 1.) LDA, HMPA, 2.) HMPA / 1.) hexane/THF, -76 -72 deg C, 13 min, then -35 deg C, 2.) -78 deg C, 15 min

10: 11 percent / sucrose, phosphate buffer, baker's yeast, 0.2 percent Triton -100 aq. / 1 h / 30 °C

11: p-TsOH*H₂O / ethanol; H₂O / 168 h / Ambient temperature

12: 4-(N,N-dimethylamino)pyridine / pyridine

13: 97 percent / LAH / diethyl ether

14: 80 percent / NaH (60 percent), n-Bu₄N⁽¹⁺⁾*I^(1-) / paraffin; tetrahydrofuran / 1 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; baker's yeast; phosphate buffer; MS (3 Angstroem); Triton -100; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; Sucrose; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; paraffin;
DOI:10.1016/S0040-4020(01)89929-4

Reference yield:

: 4328-94-3
pentane-1,3,5-triol

: 113195-16-7,113195-17-8
(4S,5R)-2-ethoxy-4-hydroxy-5-tetrahydropyranmethanol dibenzyl ether

Guidance literature:: Multi-step reaction with 10 steps

1: 98.3 g / p-TsOH*H₂O / acetone

2: 97 percent / pyridinium chlorochromate, MS (3 Angstroem) / CH₂Cl₂

3: 64 percent / p-TsOH*H₂O / CH₂Cl₂ / Heating

4: 72 percent / pyridinium dichromate, MS (3 Angstroem) / CH₂Cl₂

5: 1.) LDA, HMPA, 2.) HMPA / 1.) hexane/THF, -76 -72 deg C, 13 min, then -35 deg C, 2.) -78 deg C, 15 min

6: 11 percent / sucrose, phosphate buffer, baker's yeast, 0.2 percent Triton -100 aq. / 1 h / 30 °C

7: p-TsOH*H₂O / ethanol; H₂O / 168 h / Ambient temperature

8: 4-(N,N-dimethylamino)pyridine / pyridine

9: 97 percent / LAH / diethyl ether

10: 80 percent / NaH (60 percent), n-Bu₄N⁽¹⁺⁾*I^(1-) / paraffin; tetrahydrofuran / 1 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; baker's yeast; phosphate buffer; MS (3 Angstroem); Triton -100; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; lithium diisopropyl amide; Sucrose; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; water; acetone; paraffin;
DOI:10.1016/S0040-4020(01)89929-4