3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one

Base Information

• Chemical Name: 3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one
• CAS No.: 149836-93-1
• Molecular Formula: C₂₁H₂₉NO₄Si
• Molecular Weight: 387.551

Synonyms:3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one

Chemical Property of 3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one

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Technology Process of 3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one

There total 2 articles about 3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-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:

C14H26BNO3 (149837-25-2) + 4(S)-benzyloxy-3-methoxy-1-(trimethylsilyl)pentyne, hexacarbonyldicobal complex → 3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one (149836-93-1)

Guidance literature:

With ammonium cerium(IV) nitrate; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 20 min, rt, 20 min, 2.) acetone, rt;

DOI:10.1021/jo952092u

Reference yield:

C14H26BNO3 (149837-25-2) + 1-(trimethylsilyl)-3(R*,S*)-methoxy-4(S)-(benzyloxy)-1-pentyne (188911-98-0) → 3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one (149836-93-1)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(00)77630-1

Reference yield: 91.0%

3-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one (149836-93-1) → (2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid (145071-98-3)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; for 18h; Ambient temperature;

DOI:10.1021/jo952092u

upstream raw materials:

C₁₄H₂₆BNO₃

1-(trimethylsilyl)-3(R*,S*)-methoxy-4(S)-(benzyloxy)-1-pentyne

Downstream raw materials:

(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid

(2S,3S)-2-((R)-1-Amino-ethyl)-3-benzyloxy-butyric acid

[(1R,2S)-2-((S)-1-Benzyloxy-ethyl)-1-methyl-but-3-ynyl]-carbamic acid tert-butyl ester

(2S,3R)-2-((S)-1-Benzyloxy-ethyl)-3-tert-butoxycarbonylamino-butyric acid

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