(2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one

Base Information

• Chemical Name: (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one
• CAS No.: 1531585-35-9
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397
• Mol file: 1531585-35-9.mol

Synonyms:(2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one

Chemical Property of (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one

There total 9 articles about (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one 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: 25.0%

(4R,5R)-5-(((2R,5S)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)methyl)-4-hydroxy-3,3-dimethyldihydrofuran-2(3H)-one (1531585-30-4) → (2R,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one (1531585-34-8) + (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one (1531585-35-9)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In hexane; dichloromethane; for 1h; Overall yield = 51 %; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.tet.2013.12.012

Reference yield:

benzyl bromide (100-39-0) → (2R,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one (1531585-34-8) + (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one (1531585-35-9)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydride / tetrahydrofuran / 18 h / 0 - 20 °C

2: water; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); acetic acid / tetrahydrofuran / 16 h / 0 - 20 °C

3: copper(l) iodide / tetrahydrofuran; diethyl ether / 3 h / -40 - 20 °C

4: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / tert-butyl alcohol; water; 1,4-dioxane / 2 h

5: boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 - 20 °C

6: dicyclohexylboron chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 9 h / 90 °C / Inert atmosphere; Microwave irradiation

7: potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; osmium(VIII) oxide; potassium hexacyanoferrate(III); methanesulfonamide / tert-butyl alcohol; water / 15 h / 20 °C

8: [bis(acetoxy)iodo]benzene; iodine / dichloromethane; hexane / 1 h / Inert atmosphere; Microwave irradiation

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; sodium periodate; copper(l) iodide; osmium(VIII) oxide; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); methanesulfonamide; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; dicyclohexylboron chloride; water; iodine; sodium hydride; potassium carbonate; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 7: |Sharpless Dihydroxylation;

DOI:10.1016/j.tet.2013.12.012

Reference yield:

Benzyloxymethyl-oxiran (2930-05-4) → (2R,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one (1531585-34-8) + (2S,3a′R,5S,6a′R)-5-((benzyloxy)methyl)-6′,6′-dimethyltetrahydro-3H,3′H-spiro[furan-2,2′-furo[3,2-b]furan]-5′(3a′H)-one (1531585-35-9)

Guidance literature:

Multi-step reaction with 7 steps

1: water; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); acetic acid / tetrahydrofuran / 16 h / 0 - 20 °C

2: copper(l) iodide / tetrahydrofuran; diethyl ether / 3 h / -40 - 20 °C

3: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / tert-butyl alcohol; water; 1,4-dioxane / 2 h

4: boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 - 20 °C

5: dicyclohexylboron chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 9 h / 90 °C / Inert atmosphere; Microwave irradiation

6: potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; osmium(VIII) oxide; potassium hexacyanoferrate(III); methanesulfonamide / tert-butyl alcohol; water / 15 h / 20 °C

7: [bis(acetoxy)iodo]benzene; iodine / dichloromethane; hexane / 1 h / Inert atmosphere; Microwave irradiation

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; sodium periodate; copper(l) iodide; osmium(VIII) oxide; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); methanesulfonamide; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; dicyclohexylboron chloride; water; iodine; potassium carbonate; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 6: |Sharpless Dihydroxylation;

DOI:10.1016/j.tet.2013.12.012

upstream raw materials:

(4R,5R)-5-(((2R,5S)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)methyl)-4-hydroxy-3,3-dimethyldihydrofuran-2(3H)-one

(4R,5R)-5-(((2S,5S)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)methyl)-4-hydroxy-3,3-dimethyldihydrofuran-2(3H)-one

benzyl bromide

Benzyloxymethyl-oxiran