(S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one
• CAS No.: 1312080-52-6
• Molecular Formula: C₃₀H₄₂O₆Si
• Molecular Weight: 526.745

Synonyms:(S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one

Chemical Property of (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one

Chemical Property:

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Technology Process of (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one

There total 15 articles about (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-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: 77.0%

(5R,6R)-6-(3-((tert-butyldiphenylsilyl)oxy)propyl)-8-((2S)-2-methyl-5-oxooxolan-2-yl)-1,3,7-trioxaspiro[4.5]decan-2-one (1312080-51-5) → (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one (1312080-52-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201007757

Reference yield:

pent-1-yn-5-ol (5390-04-5) → (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one (1312080-52-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: zirconocene dichloride; water / hexane; 1,2-dichloro-ethane / -20 - 20 °C / Inert atmosphere

1.2: 0.17 h / -30 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 0.33 h / 0 °C / Inert atmosphere

2.2: 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / Reflux; Inert atmosphere

4.2: 1 h / 0 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.67 h / 0 °C / Inert atmosphere

5.2: 16 h / 20 °C / Inert atmosphere

6.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6.2: 72 h / Inert atmosphere

7.1: Oxone; borax; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one / Dimethoxymethane; water; acetonitrile / 3 h / 0 °C / Inert atmosphere

7.2: 0 - 20 °C / Inert atmosphere

8.1: sodium acetate; sodium thiosulfate; N-methyl-1-quinolinium hexafluorophosphate / 1,1-dichloroethane; toluene / 3 h / 20 °C / Molecular sieve; Irradiation

9.1: 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) / dichloromethane / 3 h / 0 °C / Inert atmosphere

9.2: 0.5 h / 0 °C / Inert atmosphere

10.1: potassium carbonate / methanol / 20 °C / Inert atmosphere

With borax; Oxone; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; zirconocene dichloride; oxalyl dichloride; water; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; sodium hydride; potassium carbonate; sodium thiosulfate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; N-methyl-1-quinolinium hexafluorophosphate; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; 1,1-dichloroethane; Dimethoxymethane; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.2: Suzuki coupling / 7.1: Shi epoxidation reaction / 7.2: Shi epoxidation reaction;

DOI:10.1002/anie.201007757

Reference yield:

tert-butyl (2E)-6-((tert-butyldiphenylsilyl)oxy)-2-iodohex-2-en-1-yl carbonate (1312080-30-0) → (S)-5-((2R,5R,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxy-5-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one (1312080-52-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

1.2: 72 h / Inert atmosphere

2.1: Oxone; borax; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one / Dimethoxymethane; water; acetonitrile / 3 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: sodium acetate; sodium thiosulfate; N-methyl-1-quinolinium hexafluorophosphate / 1,1-dichloroethane; toluene / 3 h / 20 °C / Molecular sieve; Irradiation

4.1: 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) / dichloromethane / 3 h / 0 °C / Inert atmosphere

4.2: 0.5 h / 0 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 20 °C / Inert atmosphere

With borax; Oxone; 9-borabicyclo[3.3.1]nonane dimer; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; sodium thiosulfate; 3-chloro-benzenecarboperoxoic acid; N-methyl-1-quinolinium hexafluorophosphate; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; 1,1-dichloroethane; Dimethoxymethane; dichloromethane; water; toluene; acetonitrile; 1.2: Suzuki coupling / 2.1: Shi epoxidation reaction / 2.2: Shi epoxidation reaction;

DOI:10.1002/anie.201007757

upstream raw materials:

(E)-7-methoxy-4-methyl-8,8-diphenylocta-1,3-diene

(E)-6-(tert-butyldiphenylsiloxy)-2-iodohex-2-en-1-ol

tert-butyl (2E)-6-((tert-butyldiphenylsilyl)oxy)-2-iodohex-2-en-1-yl carbonate

(2Z)-1-((tert-butyloxycarbonyl)oxy)-6-(tert-butyldiphenylsiloxy)-2-((E)-7-methoxy-4-methyl-8,8-diphenyloct-3-enyl)hex-2-ene

Downstream raw materials:

(2R,6R)-2-(3-(tert-butyldiphenylsilyloxy)propyl)-6-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)dihydro-2H-pyran-3(4H)-one

(S)-5-((2R,5S,6R)-6-(3-(tert-butyldiphenylsilyloxy)propyl)-5-hydroxytetrahydro-2H-pyran-2-yl)-5-methyldihydrofuran-2(3H)-one

(S)-((2R,3S,6R)-2-(3-(tert-butyldiphenylsilyloxy)propyl)-6-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)tetrahydro-2H-pyran-3-yl)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

(R)-((2R,3S,6R)-2-(3-(tert-butyldiphenylsilyloxy)propyl)-6-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)tetrahydro-2H-pyran-3-yl)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

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