(1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

Base Information

Chemical Name:(1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol
CAS No.:121353-37-5
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

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Chemical Property of (1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

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Technology Process of (1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

There total 16 articles about (1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-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: 83.0%

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

: 121353-37-5
(1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

Guidance literature:: With tetraethylammonium triacetoxyborohydride; acetic acid; In acetonitrile; 1.) -40 deg C, 15 min, 2.) 23 deg C, 1 h;
DOI:10.1021/jo00275a020

Reference yield:

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

: 121353-37-5
(1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

Guidance literature:: Multi-step reaction with 14 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

14: 83 percent / tetraethylammonium triacetoxyborohydride, acetic acid / acetonitrile / 1.) -40 deg C, 15 min, 2.) 23 deg C, 1 h

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

: 121353-37-5
(1S,2S,3S,4R)-4-<(1S)-1-<(benzyloxy)methyl>-1-hydroxy-2-propenyl>-3-methylcyclopentane-1,2-diol

Guidance literature:: Multi-step reaction with 12 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

12: 83 percent / tetraethylammonium triacetoxyborohydride, acetic acid / acetonitrile / 1.) -40 deg C, 15 min, 2.) 23 deg C, 1 h

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