(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

Base Information

Chemical Name:(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine
CAS No.:150943-24-1
Molecular Formula:C₂₇H₃₇NO₃Si
Molecular Weight:451.681
Hs Code.:

Synonyms:(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

Chemical Property:

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Technology Process of (2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

There total 7 articles about (2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine 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: 79.0%

: 406220-26-6
(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-(bromomethyl)methyleneazetidine

: 150943-24-1
(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 14h;
DOI:10.1139/v01-171

Reference yield:

: N-Boc-O-TBDPS-(R)-serine

: 150943-24-1
(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: isobutyl chloroformate; 4-methylmorpholine / CH₂Cl₂ / 0.75 h / -10 °C

1.2: 97 percent / CH₂Cl₂; diethyl ether / 7 h / 20 °C

2.1: 67 percent / Rh₂(OAc)4 / CH₂Cl₂ / 15 h / -95 - 20 °C

3.1: 67 percent / methanol / 25 h / -78 - 20 °C

4.1: 24 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

5.1: 80 percent / PPh₃; CBr₄ / CH₂Cl₂ / 20 °C

6.1: 79 percent / LiBH₄ / tetrahydrofuran / 14 h / 20 °C

With 4-methyl-morpholine; lithium aluminium tetrahydride; lithium borohydride; carbon tetrabromide; triphenylphosphine; isobutyl chloroformate; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1139/v01-171

Reference yield:

: 150943-16-1
(3R)-1-diazo-3-(N-tert-butyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)-2-butanone

: 150943-24-1
(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-ethylideneazetidine

Guidance literature:: Multi-step reaction with 5 steps

1: 67 percent / Rh₂(OAc)4 / CH₂Cl₂ / 15 h / -95 - 20 °C

2: 67 percent / methanol / 25 h / -78 - 20 °C

3: 24 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

4: 80 percent / PPh₃; CBr₄ / CH₂Cl₂ / 20 °C

5: 79 percent / LiBH₄ / tetrahydrofuran / 14 h / 20 °C

With lithium aluminium tetrahydride; lithium borohydride; carbon tetrabromide; triphenylphosphine; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1139/v01-171