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

Base Information

• Chemical Name: 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
• CAS No.: 1613145-04-2
• Molecular Formula: C₃₄H₄₈I₂O₆Si
• Molecular Weight: 834.646

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 3 articles about 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 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: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + (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 (1613144-99-2) → 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 (1613145-04-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 14h; Inert atmosphere;

DOI:10.1039/c4cc02702g

Reference yield:

{(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 (1613144-89-0) → 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 (1613145-04-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; triethylamine; sodium iodide; In dichloromethane; acetone;

DOI:10.1039/c4cc02702g

Reference yield:

(R)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate (501365-06-6) → 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 (1613145-04-2)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

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

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

With dmap; triethylamine; trifluoroacetic acid; sodium iodide; In dichloromethane; acetone;

DOI:10.1039/c4cc02702g

upstream raw materials:

(R)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

{(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

di-tert-butyl dicarbonate

(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

Downstream raw materials:

tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate

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

(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

(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

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