(2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

Base Information

Chemical Name:(2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine
CAS No.:260417-88-7
Molecular Formula:C₂₄H₃₈N₂O₇Si
Molecular Weight:494.66
Hs Code.:

Synonyms:(2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

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Chemical Property of (2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

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Technology Process of (2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

There total 10 articles about (2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine 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: 87.0%

: 2937-50-0
Allyl chloroformate

: 260417-87-6
(2S,4R)-N-(2-amino-4,5-dimethoxybenzoyl)-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

: 260417-88-7
(2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃;
DOI:10.1016/S0960-894X(00)00351-6

Reference yield:

: (2S)(4R)-N-(2-Amino-4,5-dimethoxybenzoyl)-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

: 2937-50-0
Allyl chloroformate

: 260417-88-7
(2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

Guidance literature:: With pyridine; In dichloromethane;

Reference yield:

: 64187-48-0
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

: 260417-88-7
(2S)(4R)-N-[(2-Allyloxycarbonylamino)-4,5-dimethoxybenzoyl]-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / LiBH₄ / tetrahydrofuran / 0 °C

2: 70 percent / TEA; DBU / CH₂Cl₂

3: 100 percent / H₂ / 10 percent Pd-C / ethanol

4: TEA / CH₂Cl₂ / 0 °C

5: 95 percent / Raney Ni; NH₂NH₂ / methanol / Heating

6: 87 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; lithium borohydride; TEA; hydrogen; nickel; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Reduction / 2: silylation / 3: Hydrogenolysis / 4: Acylation / 5: Reduction / 6: Acylation;
DOI:10.1016/S0960-894X(00)00351-6