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

Base Information

Chemical Name:(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-(bromomethyl)methyleneazetidine
CAS No.:406220-26-6
Molecular Formula:C₂₇H₃₆BrNO₃Si
Molecular Weight:530.577
Hs Code.:

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

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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-(bromomethyl)methyleneazetidine

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

There total 6 articles about (2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-(bromomethyl)methyleneazetidine 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: 80.0%

: 150943-23-0
(2S,Z)-1-tert-butyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-3-(hydroxymethyl)methyleneazetidine

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

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃;
DOI:10.1139/v01-171

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 4-methyl-morpholine; lithium aluminium tetrahydride; 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

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

Guidance literature:: Multi-step reaction with 4 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

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