(4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

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Chemical Name:(4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one
CAS No.:1613145-20-2
Molecular Formula:C₃₃H₄₅IO₆Si
Molecular Weight:692.707
Hs Code.:

Synonyms:

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Chemical Property of (4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

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Technology Process of (4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

There total 4 articles about (4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-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:

: 1613145-19-9
tert-butyl {(R)-1-[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]pent-4-en-2-yl} carbonate

: 1613145-20-2
(4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

: 1613145-21-3
(4S,6R)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

Guidance literature:: With N-iodo-succinimide; In acetonitrile; at -40 - 20 ℃; for 4.5h; Overall yield = 72 %; Overall yield = 12 mg;
DOI:10.1039/c4cc02702g

Reference yield:

: 1613144-99-2
(2S,4S,6R)-2-{[(2S,4S,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methyl}-6-(iodomethyl)tetrahydro-2H-pyran-4-ol

: 1613145-20-2
(4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

: 1613145-21-3
(4S,6R)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

2: zinc; ammonium chloride / tetrahydrofuran; water / 1 h / 70 °C / Inert atmosphere; Sealed tube

3: pyridinium p-toluenesulfonate / acetone / 3 h / 20 °C / Inert atmosphere

4: N-iodo-succinimide / acetonitrile / 4.5 h / -40 - 20 °C

With dmap; N-iodo-succinimide; pyridinium p-toluenesulfonate; ammonium chloride; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile;
DOI:10.1039/c4cc02702g

Reference yield:

: 1613145-04-2
tert-butyl {(2R,4S,6R)-2-[((2S,4S,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2Hpyran-2-yl)methyl]-6-(iodomethyl)tetrahydro-2H-pyran-4-yl} carbonate

: 1613145-20-2
(4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

: 1613145-21-3
(4S,6R)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: zinc; ammonium chloride / tetrahydrofuran; water / 1 h / 70 °C / Inert atmosphere; Sealed tube

2: pyridinium p-toluenesulfonate / acetone / 3 h / 20 °C / Inert atmosphere

3: N-iodo-succinimide / acetonitrile / 4.5 h / -40 - 20 °C

With N-iodo-succinimide; pyridinium p-toluenesulfonate; ammonium chloride; zinc; In tetrahydrofuran; water; acetone; acetonitrile;
DOI:10.1039/c4cc02702g