methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

Base Information

Chemical Name:methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate
CAS No.:927410-53-5
Molecular Formula:C₁₉H₂₆N₂O₇
Molecular Weight:394.425
Hs Code.:

Synonyms:methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

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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 methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

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Technology Process of methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

There total 5 articles about methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate 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: 70.0%

: 927410-52-4
(2R)-3-amino-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)propanoic acidmethyl ester

: 1138-80-3
N-(Benzyloxycarbonyl)glycine

: 927410-53-5
methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

Guidance literature:: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.tetasy.2006.11.037

Reference yield:

: 233758-86-6
(4R)-2,2-dimethyl-4-[(E)-2-nitrovinyl]-1,3-dioxolane

: 927410-53-5
methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

2: 69 percent / HgO; BF₃*OEt₂ / tetrahydrofuran; H₂O / 48 h / 20 °C

3: 83 percent / H₂ / Pd/C / ethyl acetate / 4 h / 20 °C

4: 70 percent / TBTU; DIPEA / CH₂Cl₂ / 12 h / 20 °C

With n-butyllithium; boron trifluoride diethyl etherate; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 1: Michael addition;
DOI:10.1016/j.tetasy.2006.11.037

Reference yield:

: 927410-51-3
methyl (2R)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3-nitropropanoate

: 927410-53-5
methyl (2R,3R)-2-{[2-(benzyloxycarbonylamino)acetamido]methyl}-3,4-(isopropylidendioxy)butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / H₂ / Pd/C / ethyl acetate / 4 h / 20 °C

2: 70 percent / TBTU; DIPEA / CH₂Cl₂ / 12 h / 20 °C

With hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1016/j.tetasy.2006.11.037