3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

Base Information

Chemical Name:3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine
CAS No.:457068-09-6
Molecular Formula:C₂₇H₃₀N₂O₇
Molecular Weight:494.544
Hs Code.:

Synonyms:3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

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Chemical Property of 3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

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Technology Process of 3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

There total 22 articles about 3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine 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%

: 3',5'-di-O-benzyl-2'-O-(2-methoxypropyl)-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

: 457068-09-6
3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

Guidance literature:: With methanol; toluene-4-sulfonic acid; In tetrahydrofuran; at 0 ℃; for 1h;

Reference yield: 85.0%

: 457068-08-5
1-[(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-(1-methoxy-1-methyl-ethoxy)-hexahydro-furo[2,3-c]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 457068-09-6
3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; at 0 ℃;
DOI:10.1016/S0040-4039(02)00784-0

Reference yield:

: 197702-06-0
3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 457068-09-6
3',5'-di-O-benzyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine

Guidance literature:: Multi-step reaction with 14 steps

1: aqueous acetic acid / 3 h / 40 °C

2: sodium periodate / tetrahydrofuran; H₂O / 0.75 h / 0 °C

3: 2.9 g / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

4: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

5: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

6: NaIO₄; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

7: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

8: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

9: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

10: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

11: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

12: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

13: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

14: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

With methanol; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; sodium hexamethyldisilazane; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; methylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3: aldol-Cannizzaro reaction;
DOI:10.1021/jo051187l