methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate

Base Information

• Chemical Name: methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate
• CAS No.: 127257-34-5
• Molecular Formula: C₂₄H₂₇N₃O₁₁
• Molecular Weight: 533.492
• Mol file: 127257-34-5.mol

Synonyms:methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate

Chemical Property of methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate

There total 51 articles about methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate 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: 85.0%

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose (154799-95-8) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate (127257-35-6) + methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate (127257-34-5)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100 ℃; for 0.5h;

DOI:10.1021/jo00299a017

Reference yield: 73.4%

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose (154799-95-8) + thymin (65-71-4,28806-14-6,691841-57-3) → methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate (127257-34-5)

Guidance literature:

thymin;

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 0.416667h; Heating;

DOI:10.1016/j.tetasy.2005.03.034

Reference yield:

C22H27NO11 → methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate (127257-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10 percent Pd-C / acetic acid / 48 h / 5320 Torr / Ambient temperature

2: NaHCO₃ / dioxane / 15 h / 0 °C

3: 75 percent / TMSOTf / CH₂Cl₂ / Heating

With trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; acetic acid;

DOI:10.1016/S0040-4039(00)78564-9

upstream raw materials:

1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

thymin

1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-2-en-1-one

Downstream raw materials:

(S)-Benzyloxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid