3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose

Base Information

Chemical Name:3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose
CAS No.:457068-01-8
Molecular Formula:C₃₃H₃₈O₈S
Molecular Weight:594.726
Hs Code.:

Synonyms:3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose

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

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

There total 5 articles about 3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-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: 93.0%

: 98-59-9
p-toluenesulfonyl chloride

: 457068-00-7
3-C-allyl-3,5-di-O-benzyl-4-C-hydroxymethyl-1,2-di-O-isopropylidene-α-D-ribofuranose

: 457068-01-8
3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 19h;
DOI:10.1021/jo051187l

Reference yield:

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

: 457068-01-8
3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 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

With dmap; sodium hydroxide; sodium periodate; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 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

: 457068-01-8
3-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

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

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

With dmap; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo051187l