1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

Base Information

Chemical Name:1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose
CAS No.:457068-03-0
Molecular Formula:C₃₅H₄₀O₁₂S
Molecular Weight:684.761
Hs Code.:

Synonyms:1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

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Chemical Property of 1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

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Technology Process of 1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

There total 14 articles about 1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose 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: 98.0%

: 108-24-7
acetic anhydride

: 457068-02-9
3,5-Di-O-benzyl-3-C-hydroxyethyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose

: 457068-03-0
1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

Guidance literature:: With sulfuric acid; In acetic acid; at 20 ℃;
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

: 457068-03-0
1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

Guidance literature:: Multi-step reaction with 8 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

With dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; sulfuric acid; water; sodium hydride; acetic acid; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: aldol-Cannizzaro reaction;
DOI:10.1021/jo051187l

Reference yield:

: 457067-99-1
3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 457068-03-0
1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

Guidance literature:: Multi-step reaction with 13 steps

1: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

2: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

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

4: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

5: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

6: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

7: 87 percent / MeNH₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

8: 90 percent / p-TsOH*H₂O / CH₂Cl₂ / 3 h / 0 °C

9: 87 percent / NaOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 - 20 °C

10: 73 percent / sodium hexamethyldisilazide / tetrahydrofuran / 6 h / Heating

11: 85 percent / MeOH; p-TsOH*H₂O / tetrahydrofuran / 1 h / 0 °C

12: 90 percent / DBU / dimethylformamide / 0.75 h / 0 °C

13: 86 percent / sodium hydride / dimethylformamide / 1 h / 20 °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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; methylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo051187l