(2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

Base Information

Chemical Name:(2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone
CAS No.:121353-31-9
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

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Chemical Property of (2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

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Technology Process of (2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

There total 15 articles about (2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone 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:

: 121353-24-0
(2S,3S)-2-methyl-3-<1(E)-propenyl>cyclopentanone

: 121353-31-9
(2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

Guidance literature:: Multi-step reaction with 13 steps

1: 84 percent / p-toluenesulfonic acid monohydrate / benzene / 7 h / Heating

2: N-methylmorpholine N-oxide monohydrate, osmium tetraoxide / acetone; H₂O; 2-methyl-propan-2-ol / 2 h / 23 °C

3: 95 percent / sodium periodate / dioxane; H₂O / 1 h / 23 °C

4: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 10 min, 2.) -78 deg C, 1 h

5: 94 percent / pyridine, chromium trioxide, molecular sieves 4A / CH₂Cl₂ / 0.5 h / 23 °C

6: H₂ / 10percent Pd/C / ethanol / 60 h / 23 °C

7: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 15 min, 2.) THF, 23 deg C, 1 h

8: 96 percent / D-(-)-diethyl tartrate ((-)-DET), molecular sieves 4A, titanium(IV) isopropoxide, tert-butyl hydroperoxide (TBHP) / CH₂Cl₂ / 5 h / -20 °C

9: 1.) potassium hydride / 1.) THF, 23 deg C, 20 min, 2.) 23 deg C, 32 h

10: 93 percent / triethylamine, sulfur trioxide pyridine complex / dimethylsulfoxide / 1 h / 23 °C

11: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 20 min, 2.) 50 deg C, 48 h

12: 100 percent / iron(III) chloride / acetone / 5 h / 23 °C

13: 1.) LDA, 2.) oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) (MoOPH) / 1.) THF/hexane, -78 deg C, 30 min, 2.) -30 deg C, 10 min

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; MoO₅*pyridine*HMPA; diethyl (2S,3S)-tartrate; 4 A molecular sieve; potassium tert-butylate; hydrogen; sulfur trioxide pyridine complex; iron(III) chloride; potassium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jo00275a020

Reference yield:

: 121353-44-4
1-((6S,7R)-6-Methyl-1,4-dioxa-spiro[4.4]non-7-yl)-propane-1,2-diol

: 121353-31-9
(2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / sodium periodate / dioxane; H₂O / 1 h / 23 °C

2: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 10 min, 2.) -78 deg C, 1 h

3: 94 percent / pyridine, chromium trioxide, molecular sieves 4A / CH₂Cl₂ / 0.5 h / 23 °C

4: H₂ / 10percent Pd/C / ethanol / 60 h / 23 °C

5: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 15 min, 2.) THF, 23 deg C, 1 h

6: 96 percent / D-(-)-diethyl tartrate ((-)-DET), molecular sieves 4A, titanium(IV) isopropoxide, tert-butyl hydroperoxide (TBHP) / CH₂Cl₂ / 5 h / -20 °C

7: 1.) potassium hydride / 1.) THF, 23 deg C, 20 min, 2.) 23 deg C, 32 h

8: 93 percent / triethylamine, sulfur trioxide pyridine complex / dimethylsulfoxide / 1 h / 23 °C

9: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 20 min, 2.) 50 deg C, 48 h

10: 100 percent / iron(III) chloride / acetone / 5 h / 23 °C

11: 1.) LDA, 2.) oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) (MoOPH) / 1.) THF/hexane, -78 deg C, 30 min, 2.) -30 deg C, 10 min

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; n-butyllithium; MoO₅*pyridine*HMPA; diethyl (2S,3S)-tartrate; 4 A molecular sieve; potassium tert-butylate; hydrogen; sulfur trioxide pyridine complex; iron(III) chloride; potassium hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jo00275a020

Reference yield:

: 121422-62-6
(6S,7R)-6-Methyl-1,4-dioxa-spiro[4.4]nonane-7-carbaldehyde

: 121353-31-9
(2S,3R,5S)-3-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-5-hydroxy-2-methylcyclopentanone

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 10 min, 2.) -78 deg C, 1 h

2: 94 percent / pyridine, chromium trioxide, molecular sieves 4A / CH₂Cl₂ / 0.5 h / 23 °C

3: H₂ / 10percent Pd/C / ethanol / 60 h / 23 °C

4: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 15 min, 2.) THF, 23 deg C, 1 h

5: 96 percent / D-(-)-diethyl tartrate ((-)-DET), molecular sieves 4A, titanium(IV) isopropoxide, tert-butyl hydroperoxide (TBHP) / CH₂Cl₂ / 5 h / -20 °C

6: 1.) potassium hydride / 1.) THF, 23 deg C, 20 min, 2.) 23 deg C, 32 h

7: 93 percent / triethylamine, sulfur trioxide pyridine complex / dimethylsulfoxide / 1 h / 23 °C

8: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 20 min, 2.) 50 deg C, 48 h

9: 100 percent / iron(III) chloride / acetone / 5 h / 23 °C

10: 1.) LDA, 2.) oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) (MoOPH) / 1.) THF/hexane, -78 deg C, 30 min, 2.) -30 deg C, 10 min

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; MoO₅*pyridine*HMPA; diethyl (2S,3S)-tartrate; 4 A molecular sieve; potassium tert-butylate; hydrogen; sulfur trioxide pyridine complex; iron(III) chloride; potassium hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1021/jo00275a020