[(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene

Base Information

• Chemical Name: [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene
• CAS No.: 388602-47-9
• Molecular Formula: C₂₄H₄₂O₂Si₂
• Molecular Weight: 418.767

Synonyms:[(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene

Chemical Property of [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene

Chemical Property:

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Technology Process of [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene

There total 3 articles about [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene 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: 87.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3R,4R)-(+)-1-benzyloxy-2,4-dimethyl-6-trimethylsilyl-5-hexyn-3-ol (388602-46-8) → [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene (388602-47-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ol016899m

Reference yield:

(2S)-3-(benzyloxy)-2-methylpropanal (79027-28-4) → [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene (388602-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / HMPA; InI / Pd(OAc)2*PPh₃ / tetrahydrofuran / 0.25 h / 0 °C

2: 87 percent / Et₃N / CH₂Cl₂ / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; indium iodide; triethylamine; Pd(PPh₃)(OAc)2; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016899m

Reference yield:

(S)-4-trimethylsilyl-3-butyn-2-yl mesylate (375395-74-7) → [(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-6-trimethylsilanyl-hex-5-ynyloxymethyl]-benzene (388602-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / HMPA; InI / Pd(OAc)2*PPh₃ / tetrahydrofuran / 0.25 h / 0 °C

2: 87 percent / Et₃N / CH₂Cl₂ / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; indium iodide; triethylamine; Pd(PPh₃)(OAc)2; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016899m

upstream raw materials:

t-butyldimethylsiyl triflate

(2S,3R,4R)-(+)-1-benzyloxy-2,4-dimethyl-6-trimethylsilyl-5-hexyn-3-ol

(2S)-3-(benzyloxy)-2-methylpropanal

(S)-4-trimethylsilyl-3-butyn-2-yl mesylate

Downstream raw materials:

[(E)-(1S,2S)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-dec-5-en-3-ynyloxy]-tert-butyl-dimethyl-silane

[(E)-(1S,2S)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-dec-5-en-3-ynyloxy]-dimethyl-silane

(4R,5R)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(E)-hept-2-en-(E)-ylidene]-2,2,4-trimethyl-[1,2]oxasilolane

(2S,3R,4R,7E)-(-)-1-benzyloxy-2,4-dimethyl-7-dodecen-5-yn-3-ol

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