(3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone
• CAS No.: 97764-65-3
• Molecular Formula: C₂₃H₄₁NO₄Si₂
• Molecular Weight: 451.754

Synonyms:(3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

Chemical Property of (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

Chemical Property:

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Technology Process of (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone

There total 4 articles about (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone 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: 77.5%

2,4-bis(O-tert-butyldimethylsilyl)-L-threonic acid (benzyloxy)amide (97764-63-1) → (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone (97764-65-3)

Guidance literature:

With triethylamine; triphenylphosphine; In tetrachloromethane; acetonitrile; Ambient temperature;

DOI:10.1021/jo00219a009

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone (97764-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73.5 percent / pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 4 h, 2.) RT, overnight

2: 77.5 percent / triphenylphosphine, NEt₃ / acetonitrile; CCl₄ / Ambient temperature

With pyridine; triethylamine; triphenylphosphine; In tetrachloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jo00219a009

Reference yield:

L-threonic acid (benzyloxy)amide (97764-61-9) → (3R,4S)-1-(benzyloxy)-3-<(tert-butyldimethylsilyl)oxy>-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone (97764-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73.5 percent / pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 4 h, 2.) RT, overnight

2: 77.5 percent / triphenylphosphine, NEt₃ / acetonitrile; CCl₄ / Ambient temperature

With pyridine; triethylamine; triphenylphosphine; In tetrachloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jo00219a009

upstream raw materials:

2,4-bis(O-tert-butyldimethylsilyl)-L-threonic acid (benzyloxy)amide

tert-butyldimethylsilyl chloride

L-threonic acid (benzyloxy)amide

2,4-O,N-tris(tert-butyldimethylsilyl)-L-threonic acid (benzyloxy)amide

Downstream raw materials:

(3R,4S)-1-(benzyloxy)-3-hydroxy-4-(hydroxymethyl)-2-azetidinone

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