(3S,5S)-5-(iodomethyl)-3-[2-(t-butyldiphenylsilyloxy)ethyl]-2,6-dioxacyclohexanone

Base Information

• Chemical Name: (3S,5S)-5-(iodomethyl)-3-[2-(t-butyldiphenylsilyloxy)ethyl]-2,6-dioxacyclohexanone
• CAS No.: 116996-55-5
• Molecular Formula: C₂₃H₂₉IO₄Si
• Molecular Weight: 524.471
• Mol file: 116996-55-5.mol

Synonyms:(3S,5S)-5-(iodomethyl)-3-[2-(t-butyldiphenylsilyloxy)ethyl]-2,6-dioxacyclohexanone

Chemical Property of (3S,5S)-5-(iodomethyl)-3-[2-(t-butyldiphenylsilyloxy)ethyl]-2,6-dioxacyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-5-(iodomethyl)-3-[2-(t-butyldiphenylsilyloxy)ethyl]-2,6-dioxacyclohexanone

There total 10 articles about (3S,5S)-5-(iodomethyl)-3-[2-(t-butyldiphenylsilyloxy)ethyl]-2,6-dioxacyclohexanone 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:

(2S)-4-O-(tert-butyldiphenylsilyl)butane-1,2,4-triol (116996-52-2) → 4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-iodomethyl-[1,3]dioxan-2-one (116996-55-5,126060-84-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / pyridine / CH₂Cl₂ / 1.) -30 deg C, 3 h, 2.) RT, 40 h

2: 91 percent / BnMe₃N⁽¹⁺⁾*OH^(1-) / methanol; diethyl ether / 0.5 h / Ambient temperature

3: 1.) CuCN / 1.) THF, -60 deg C, 2.) -10 deg C, 4 h

With pyridine; N-benzyl-trimethylammonium hydroxide; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00164a024

Reference yield:

tert-Butyl-[2-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-ethoxy]-diphenyl-silane (116996-51-1) → 4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-iodomethyl-[1,3]dioxan-2-one (116996-55-5,126060-84-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / 80percent aq. AcOH / 4 h / 50 °C

2: 68 percent / pyridine / CH₂Cl₂ / 1.) -30 deg C, 3 h, 2.) RT, 40 h

3: 91 percent / BnMe₃N⁽¹⁺⁾*OH^(1-) / methanol; diethyl ether / 0.5 h / Ambient temperature

4: 1.) CuCN / 1.) THF, -60 deg C, 2.) -10 deg C, 4 h

With pyridine; N-benzyl-trimethylammonium hydroxide; acetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00164a024

Reference yield:

Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl ester (116996-53-3) → 4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-iodomethyl-[1,3]dioxan-2-one (116996-55-5,126060-84-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / BnMe₃N⁽¹⁺⁾*OH^(1-) / methanol; diethyl ether / 0.5 h / Ambient temperature

2: 1.) CuCN / 1.) THF, -60 deg C, 2.) -10 deg C, 4 h

With N-benzyl-trimethylammonium hydroxide; In methanol; diethyl ether;

DOI:10.1021/ja00164a024

upstream raw materials:

carbon dioxide

(3R)-1-(tert-butyldiphenylsilyloxy)hex-5-en-3-ol

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

(2S)-4-O-(tert-butyldiphenylsilyl)butane-1,2,4-triol

Downstream raw materials:

(4S-cis)-(1,1-dimethylethyl)<2-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethoxy>diphenylsilane

3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde

<1S-<1α,4α-(4S^*,6R^*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one

(2S,4S)-(6-O-t-butyldiphenylsilyl)-1,2-epoxyhexa-4,6-diol