(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

Base Information

Chemical Name:(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran
CAS No.:925683-97-2
Molecular Formula:C₂₂H₃₆O₅S₂Si
Molecular Weight:472.742
Hs Code.:

Synonyms:(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

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Chemical Property of (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

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Technology Process of (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

There total 6 articles about (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran 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: 78.0%

: 75-15-0,12122-00-8
carbon disulfide

: 925683-96-1
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

: 74-88-4
methyl iodide

: 925683-97-2
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

Guidance literature:: carbon disulfide; (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol; With sodium hydride; for 4h;

methyl iodide; for 12h; Further stages.;
DOI:10.1055/s-2006-950325

Reference yield:

: 6752-48-3
(4aR,6S,8R,8aS)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

: 925683-97-2
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating

2.1: 79 percent / PTSA / methanol / 12 h

3.1: 83 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

4.1: NaH / 4 h

4.2: 78 percent / 12 h

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-2006-950325

Reference yield:

: 6087-40-7
(2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran

: 925683-97-2
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaOMe / methanol / 1 h / 20 °C

2.1: 7.4 g / PTSA / toluene / 6 h / Heating

3.1: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating

4.1: 79 percent / PTSA / methanol / 12 h

5.1: 83 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

6.1: NaH / 4 h

6.2: 78 percent / 12 h

With 1H-imidazole; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1055/s-2006-950325