1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione

Base Information

• Chemical Name: 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione
• CAS No.: 78137-99-2
• Molecular Formula: C₂₄H₂₇N₃O₆
• Molecular Weight: 453.495
• Mol file: 78137-99-2.mol

Synonyms:

Chemical Property of 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione

There total 10 articles about 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione 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: 10.0%

4-Methyl-benzoic acid (2R,3S)-2-benzyloxymethyl-5-chloro-tetrahydro-furan-3-yl ester (78138-11-1,78138-14-4) + 1-methyl-4,6-bis-trimethylsilanyloxy-1,2-dihydro-[1,3,5]triazine (66515-67-1) → 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione (78137-98-1) + 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione (78137-99-2)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; acetonitrile; at -30 ℃; for 2h;

DOI:10.1016/S0008-6215(00)85610-4

Reference yield:

benzyl bromide (100-39-0) → 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione (78137-99-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 42 percent / silver(I) oxide, diisopropylethylamine / toluene / 18 h / 50 °C

2: 63 percent / 80percent aq. acetic acid / 0.33 h / Heating

3: 90 percent / pyridine / 1 h / 50 °C

4: hydrogen chloride / diethyl ether / 0.5 h / 5 °C

5: 10 percent / stannic chloride / acetonitrile; 1,2-dichloro-ethane / 2 h / -30 °C

With hydrogenchloride; tin(IV) chloride; acetic acid; N-ethyl-N,N-diisopropylamine; silver(l) oxide; pyridine; In diethyl ether; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)85610-4

Reference yield:

4-methyl-benzoyl chloride (874-60-2) → 1-<5-O-benzyl-3-O-(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl>-5,6-dihydro-5-N-methyl-s-triazine-2,4-(3H)-dione (78137-99-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / pyridine / 18 h / Ambient temperature

2: 71 percent / trifluoroacetic acid / CHCl₃ / 0.25 h

3: 42 percent / silver(I) oxide, diisopropylethylamine / toluene / 18 h / 50 °C

4: 63 percent / 80percent aq. acetic acid / 0.33 h / Heating

5: 90 percent / pyridine / 1 h / 50 °C

6: hydrogen chloride / diethyl ether / 0.5 h / 5 °C

7: 10 percent / stannic chloride / acetonitrile; 1,2-dichloro-ethane / 2 h / -30 °C

With hydrogenchloride; tin(IV) chloride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; silver(l) oxide; pyridine; In pyridine; diethyl ether; chloroform; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1016/S0008-6215(00)85610-4

upstream raw materials:

4-Methyl-benzoic acid (2R,3S)-2-benzyloxymethyl-5-chloro-tetrahydro-furan-3-yl ester

1-methyl-4,6-bis-trimethylsilanyloxy-1,2-dihydro-[1,3,5]triazine

benzyl bromide

4-methyl-benzoyl chloride