tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane

Base Information

• Chemical Name: tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane
• CAS No.: 1643685-85-1
• Molecular Formula: C₃₈H₇₀O₆SSi₂
• Molecular Weight: 711.207

Synonyms:tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane

Chemical Property of tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane

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Technology Process of tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane

There total 17 articles about tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane 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: 93.0%

t-butyldimethylsiyl triflate (69739-34-0) + (3S,4R,6S)-6-{[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-3-[(S)-1-hydroxyhexyl]-2-methoxytetrahydro-2H-pyran-4-ol (1643685-84-0) → tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane (1643685-85-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.201400145

Reference yield:

(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one (1643685-75-9) → tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane (1643685-85-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

2.1: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: iodine / acetonitrile / -20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / acetone; water / 96 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

5.2: 1.5 h / 50 °C / Inert atmosphere

6.1: n-butyllithium; diisopropylamine / diethyl ether; hexane / 3 h / -78 °C / Inert atmosphere

6.2: 24 h / -78 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / toluene; hexane / -78 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / 20 °C / Inert atmosphere

9.1: potassium hydride / 0 °C / Inert atmosphere

10.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;

DOI:10.1002/ejoc.201400145

Reference yield:

(4S,6S)-4-{[(4R,4R)-4-(dimethylphenylsilyl)-6-oxo-3,4,5,6-tetrahydro-2H-pyran-2-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one (1643685-77-1) → tert-butyl [((S)-1-{(3S,4R,6R)-4-(tert-butyldimethylsilyloxy)-6-[(4S,6S)-2,2-dimethyl-6-(phenylsulfanylmethyl)-1,3-dioxan-4-yl]methyl}-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-3-yl)hexyloxy]dimethylsilane (1643685-85-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: toluene-4-sulfonic acid / acetone; water / 96 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 1.5 h / 50 °C / Inert atmosphere

3.1: n-butyllithium; diisopropylamine / diethyl ether; hexane / 3 h / -78 °C / Inert atmosphere

3.2: 24 h / -78 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / toluene; hexane / -78 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / 20 °C / Inert atmosphere

6.1: potassium hydride / 0 °C / Inert atmosphere

7.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil;

DOI:10.1002/ejoc.201400145

upstream raw materials:

(4S,6R)-6-[(ethenesulfonyl)oxy]nona-1,8-dien-4-yl (E)-but-2-enoate

(S)-6-{[(R)-2,2-dioxo-5,6-dihydro-1,2-oxathiin-6-yl]methyl}-5,6-dihydro-2H-pyran-2-one

(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

(4R,6R)-4-(dimethylphenylsilyl)-6-[(R)-2-hydroxypent-4-en-1-yl]-3,4,5,6-tetrahydro-2H-pyran-2-one

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