3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

Base Information

Chemical Name:3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose
CAS No.:69827-91-4
Molecular Formula:C₂₃H₂₈O₅
Molecular Weight:384.472
Hs Code.:

Synonyms:3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

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Chemical Property of 3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

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Technology Process of 3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

There total 21 articles about 3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-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: 42.0%

: 3-deoxy-3-C-hydroxymethyl-1,2-O-isopropylidene-5-O-pivaloyl-α-D-ribofuranose

: 100-39-0
benzyl bromide

: 69827-91-4
3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

: C₂₁H₃₀O₆

Guidance literature:: With tetrabutylammomium bromide; sodium hydroxide; In tert-butyl methyl ether; at 20 ℃; for 18h;
DOI:10.1021/ol502383c

Reference yield: 18.0%

: C₂₁H₃₀O₆

: 100-39-0
benzyl bromide

: 69827-91-4
3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

Guidance literature:: With tetrabutylammomium bromide; sodium hydroxide; In tert-butyl methyl ether; at 20 ℃; for 18h;
DOI:10.1021/ol502383c

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 69827-91-4
3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / pyridine / CHCl₃ / Ambient temperature

2: 81 percent / Na / 15 h / 100 °C

3: CrO₃, pyridine, Celite / CH₂Cl₂ / 2 h

4: 80 percent / tetrahydrofuran / 1) RT, 1 h, 2) 55 deg C, 2 h

5: 1.) BH₃*THF, 2.) 30percent aq. H₂O₂, 2 M aq. NaOH / 1.) RT, 1 h, 2.) THF, RT, 65 min

6: 1.) NaH, DMSO / 1.) 40 deg C, 1 h, 2.) RT, 50 min

With pyridine; chromium(VI) oxide; sodium hydroxide; borane-THF; Celite; dihydrogen peroxide; sodium; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/jm00061a013