(1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol

Base Information

• Chemical Name: (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol
• CAS No.: 159656-59-4
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401

Synonyms:(1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol

Chemical Property of (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol

There total 13 articles about (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol 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: 100.0%

(3S,4S,4aS,5R,7aR)-5-benzyloxy-3,4-isopropylidenedioxyoctahydrocyclopentapyran-2-ol → (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol (159656-59-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; for 1h; Ambient temperature;

Reference yield:

(2R)-6-hydroxy-2-<4'-(trimethylsilyl)but-3'-ynyl>-3,6-dihydropyran-3(2H)-one (144708-87-2) → (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol (159656-59-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 62 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂ / 5 h / Ambient temperature

2: 92 percent / LAH / diethyl ether / 0 °C

3: 70 percent / pyridine, osmium tetraoxide / diethyl ether / 10 h / Ambient temperature

4: 74 percent / PPTS / dimethylformamide; acetone / 10 h / Ambient temperature

5: 68 percent / DMAP / 1,2-dichloro-ethane / 5 h / Heating

6: 92 percent / Bu₃SnH, AIBN / benzene / 0.5 h / Heating

7: 86 percent / pyridine, NaIO₄, osmium tetraoxide / 2-methyl-propan-2-ol; H₂O / 4.5 h / Ambient temperature

8: 55 percent / Na / tetrahydrofuran; ethanol; liquid ammonia / 1.) -78 deg C, 20 min, 2.) room temperature, 1 h

9: 98 percent / NaH, Bu₄NI / tetrahydrofuran; paraffin / 15 h / Ambient temperature

10: 98 percent / HCl / tetrahydrofuran / 2 h / Ambient temperature

11: 100 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ammonia; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; paraffin; tert-butyl alcohol; benzene;

Reference yield:

(2R,6R)-6-(1-ethoxyethoxy)-2-<4'-(trimethylsilyl)but-3'-ynyl>-3,6-dihydropyran-3(2H)-one → (1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>cyclopentanol (159656-59-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / LAH / diethyl ether / 0 °C

2: 70 percent / pyridine, osmium tetraoxide / diethyl ether / 10 h / Ambient temperature

3: 74 percent / PPTS / dimethylformamide; acetone / 10 h / Ambient temperature

4: 68 percent / DMAP / 1,2-dichloro-ethane / 5 h / Heating

5: 92 percent / Bu₃SnH, AIBN / benzene / 0.5 h / Heating

6: 86 percent / pyridine, NaIO₄, osmium tetraoxide / 2-methyl-propan-2-ol; H₂O / 4.5 h / Ambient temperature

7: 55 percent / Na / tetrahydrofuran; ethanol; liquid ammonia / 1.) -78 deg C, 20 min, 2.) room temperature, 1 h

8: 98 percent / NaH, Bu₄NI / tetrahydrofuran; paraffin / 15 h / Ambient temperature

9: 98 percent / HCl / tetrahydrofuran / 2 h / Ambient temperature

10: 100 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ammonia; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; paraffin; tert-butyl alcohol; benzene;

upstream raw materials:

(2R)-6-hydroxy-2-<4'-(trimethylsilyl)but-3'-ynyl>-3,6-dihydropyran-3(2H)-one

(1R)-1-(2'-furyl)-5-(trimethylsilyl)pent-4-yn-1-ol

Downstream raw materials:

(1R,2R,3R)-3-benzyloxy-2-<(1'S,2'R)-3'-(tert-butyldimethylsiloxy)-1',2'-(isopropylidenedioxy)propyl>cyclopentanol

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

(5R,6R)-5-benzyloxy-6-<(1'S,2'R)-3'-hydroxy-1',2'-(isopropylidenedioxy)propyl>piperidin-2-one

(3aR,9R,9aR,9bS)-9-benzyloxy-2,2-dimethylhexahydro-[1,3]dioxolo[4,5-a]indolizin-6(9bH)-one

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