Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

Base Information

Chemical Name:Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester
CAS No.:186839-95-2
Molecular Formula:C₂₅H₃₃BrN₂O₈Si
Molecular Weight:597.535
Hs Code.:

Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

Synonyms:Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

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Chemical Property of Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

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Technology Process of Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

There total 6 articles about Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester 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: 86.0%

: 22118-09-8
2-bromoacetyl chloride

: 186839-93-0
3-Benzyloxymethyl-1-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

: 186839-95-2
Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane;
DOI:10.1021/jo961665f

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 186839-95-2
Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / DBU / dimethylformamide / 0.5 h / 0 °C

2: 89 percent / AgNO₃, Py / tetrahydrofuran / 24 h / Ambient temperature

3: 80 percent / CrO₃, molecular sieves, Py, Ac₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 68 percent / aq. TFA / 0.5 h / 0 °C

5: 86 percent / 2,6-lutidine / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; molecular sieve; acetic anhydride; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo961665f

Reference yield:

: 58-96-8
uridine

: 186839-95-2
Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / DBU / dimethylformamide / 0.5 h / 0 °C

2: 89 percent / AgNO₃, Py / tetrahydrofuran / 24 h / Ambient temperature

3: 80 percent / CrO₃, molecular sieves, Py, Ac₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 68 percent / aq. TFA / 0.5 h / 0 °C

5: 86 percent / 2,6-lutidine / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; molecular sieve; acetic anhydride; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo961665f