(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

Base Information

Chemical Name:(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
CAS No.:1613144-99-2
Molecular Formula:C₂₉H₄₀I₂O₄Si
Molecular Weight:734.529
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (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

There total 9 articles about (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 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: 91.0%

: 1613144-89-0
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4S,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 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

Guidance literature:: With sodium iodide; In acetone; at 120 ℃; for 2h; Microwave irradiation; Inert atmosphere; Sealed tube;
DOI:10.1021/acs.joc.5b01323

Reference yield:

: 118629-75-7
(S)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

: 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

Guidance literature:: Multi-step reaction with 6 steps

1.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

1.2: 3 h / 20 °C / pH > 7 / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; methanol / 16 h / 20 °C / 760.05 Torr

4.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

6.1: sodium iodide / acetone / 2 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube

With 1H-imidazole; tetrapropylammonium perruthennate; palladium 10% on activated carbon; hydrogen; 4-methylmorpholine N-oxide; trifluoroacetic acid; sodium iodide; In methanol; dichloromethane; ethyl acetate; acetone;
DOI:10.1021/acs.joc.5b01323

Reference yield:

: {(2S,4S,6S)-6-[2-(benzyloxy)ethyl]-4-[(tertbutyldiphenylsilyl)oxy]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; methanol / 16 h / 20 °C / 760.05 Torr

2.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

4.1: sodium iodide / acetone / 2 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube

With tetrapropylammonium perruthennate; palladium 10% on activated carbon; hydrogen; 4-methylmorpholine N-oxide; trifluoroacetic acid; sodium iodide; In methanol; dichloromethane; ethyl acetate; acetone;
DOI:10.1021/acs.joc.5b01323