[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

Base Information

Chemical Name:[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone
CAS No.:214041-46-0
Molecular Formula:C₃₀H₃₁NO₇
Molecular Weight:517.579
Hs Code.:

Synonyms:[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

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Chemical Property of [2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

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Technology Process of [2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

There total 5 articles about [2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone 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: 44.0%

: 214041-52-8
Acetic acid (2R,4aR,5S,6S,7R,7aS)-6,7-bis-benzyloxy-5-methoxyamino-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-4a-yl ester

: 214041-46-0
[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

Guidance literature:: With lead(IV) acetate; In benzene; at 20 - 40 ℃; for 40h;
DOI:10.1021/jo980485y

Reference yield:

: 20770-84-7,113566-69-1,113566-70-4
2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose

: 214041-46-0
[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

Guidance literature:: Multi-step reaction with 5 steps

1: 3.52 g / pyridine / 24 h / 40 - 45 °C

2: 1.14 g / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

3: 84 percent / t-BuOH; SmI₂ / tetrahydrofuran / -78 - 20 °C

4: 1.78 g / pyridine; DMAP / 20 °C

5: 44 percent / Pb(OAc)4 / benzene / 40 h / 20 - 40 °C

With pyridine; lead(IV) acetate; dmap; samarium diiodide; Dess-Martin periodane; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; benzene; 1: Condensation / 2: Dess-Martin oxidation / 3: Cyclization / 4: Acetylation / 5: Oxidation;
DOI:10.1021/jo980485y

Reference yield:

: 4,6-O-benzylidene-2,3-O-bis(phenylmethyl)-1-(O-methyloxime)-D-xylo-hexos-5-ulose

: 214041-46-0
[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / t-BuOH; SmI₂ / tetrahydrofuran / -78 - 20 °C

2: 1.78 g / pyridine; DMAP / 20 °C

3: 44 percent / Pb(OAc)4 / benzene / 40 h / 20 - 40 °C

With pyridine; lead(IV) acetate; dmap; samarium diiodide; tert-butyl alcohol; In tetrahydrofuran; benzene; 1: Cyclization / 2: Acetylation / 3: Oxidation;
DOI:10.1021/jo980485y