(S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

Base Information

Chemical Name:(S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one
CAS No.:287400-74-2
Molecular Formula:C₄₄H₇₄O₇Si₂
Molecular Weight:771.238
Hs Code.:

(S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

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Chemical Property of (S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

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Technology Process of (S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

There total 11 articles about (S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-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: 10.8%

: 287400-72-0
[(R)-1-(2,2-Bis-trimethylsilanyloxy-vinyloxy)-ethyl]-benzene

: (3R,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-ol

: 287400-90-2
(S)-methylbenzyloxyacetic acid

: 287400-97-9
(R)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

: 287400-74-2
(S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

Guidance literature:: Multistep reaction;
DOI:10.1021/jo0002801

Reference yield:

: 1445-91-6
(S)-1-phenylethanol

: 287400-74-2
(S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / KH / tetrahydrofuran / 20 h / Heating

2: LiHMDS / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

4: LiHMDS / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

5: 8.2 percent

With potassium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; 1: Alkylation / 2: silylation / 4: silylation;
DOI:10.1021/jo0002801

Reference yield:

: 1517-69-7
(R)-1-phenylethanol

: 287400-74-2
(S)-1-[(2R,3S,4R,5R,6R)-5-(4-Methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-1-((S)-1-phenyl-ethoxy)-propan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 98 percent / KH / tetrahydrofuran / 20 h / Heating

2.1: LiHMDS / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

4.1: LiHMDS / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

5.1: CF₃COOH; DMAP; pyridine / CH₂Cl₂

5.2: ZnBr₂

6.1: DCC; HOAT; Et₃N / dimethylformamide

7.1: tetrahydrofuran

With pyridine; dmap; 1-hydroxy-7-aza-benzotriazole; potassium hydride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: silylation / 4.1: silylation / 5.1: Acylation / 5.2: Condensation / 6.1: Substitution / 7.1: Addition;
DOI:10.1021/jo0002801