3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane

Base Information

• Chemical Name: 3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane
• CAS No.: 113195-29-2
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429
• Mol file: 113195-29-2.mol

Synonyms:

Chemical Property of 3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane

There total 31 articles about 3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane 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: 98.0%

Toluene-4-sulfonic acid (3R,6R,9R,10S)-9-benzyloxymethyl-10-hydroxy-1,7-dioxa-spiro[5.5]undec-3-ylmethyl ester (96239-87-1) → (3R,4S,6R,9R)-3-Benzyloxymethyl-9-ethyl-1,7-dioxa-spiro[5.5]undecan-4-ol (113195-29-2,113299-81-3,113299-82-4)

Guidance literature:

In diethyl ether; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)98454-5

Reference yield:

3-oxopentanedioic acid dimethyl ester (1830-54-2) → 3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane (113195-29-2,113299-81-3,113299-82-4)

Guidance literature:

Multi-step reaction with 17 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

15: acetonitrile / 1 h / Heating

16: 1.) HMPA, n-BuLi / 1.) THF/n-hexane, -67 deg C, 30 min, 2.) THF, -67 -63 deg C, then room temperature, 3 h 50 min and 6 h 15 min

17: HCl, H₂O / tetrahydrofuran / 15 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; baker's yeast; phosphate buffer; MS (3 Angstroem); Triton -100; water; 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; acetonitrile; paraffin;

DOI:10.1016/S0040-4020(01)89929-4

Reference yield:

pentane-1,3,5-triol (4328-94-3) → 3-benzyloxymethyl-9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane (113195-29-2,113299-81-3,113299-82-4)

Guidance literature:

Multi-step reaction with 13 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

11: acetonitrile / 1 h / Heating

12: 1.) HMPA, n-BuLi / 1.) THF/n-hexane, -67 deg C, 30 min, 2.) THF, -67 -63 deg C, then room temperature, 3 h 50 min and 6 h 15 min

13: HCl, H₂O / tetrahydrofuran / 15 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; baker's yeast; phosphate buffer; MS (3 Angstroem); Triton -100; water; 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; acetonitrile; paraffin;

DOI:10.1016/S0040-4020(01)89929-4

upstream raw materials:

Toluene-4-sulfonic acid (3R,6R,9R,10S)-9-benzyloxymethyl-10-hydroxy-1,7-dioxa-spiro[5.5]undec-3-ylmethyl ester

(3R,4S,6R,9S)-3-Benzyloxymethyl-9-hydroxymethyl-1,7-dioxa-spiro[5.5]undecan-4-ol

4-benzyloxy-5-benzyloxymethyl-2-<(3'-tetrahydropyranyloxymethyl)pentylidene>tetrahydropyran

3-oxopentanedioic acid dimethyl ester

Downstream raw materials:

(+/-)-talaromycin A

4-(3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undecyl) benzoate

4-(3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undecyl) benzoate

4-(3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undecyl) benzoate