Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester
CAS No.:120567-34-2
Molecular Formula:C₂₁H₂₂O₅
Molecular Weight:354.403
Hs Code.:

Synonyms:Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

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Chemical Property of Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

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Technology Process of Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

There total 12 articles about Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester 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: 100.0%

: Benzoic acid (2S,3R,4S)-2-benzyloxymethyl-4-(1-hydroxy-ethyl)-oxetan-3-ylmethyl ester

: 120567-34-2
Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -30 - -8 ℃; for 1.5h;
DOI:10.1016/S0040-4039(00)80595-X

Reference yield:

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

: 120567-34-2
Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 13 steps

2: 83 percent / 18 h / Ambient temperature

4: 88 percent / (nBu)4NF / tetrahydrofuran / 4 h / 0 °C

5: 88 percent / NaH / tetrahydrofuran / 20 h

6: 1) RhCl(PPh₃)3-DABCO; 2) HgCl₂-HgO / 1) aq. EtOH, reflux 5 h; 2) acetone-H₂O, room temp., 30 min

7: 1) Swern oxidation; 2) Et₂O, 0 degC, 2 h

8: H₂ / Pd-black / methanol / 2 h / Ambient temperature

9: TsOH / various solvent(s) / Ambient temperature

10: NaH / dimethylformamide / 2 h / 0 deg C -> room temp.

11: 83 percent / 2N HCl / dioxane / 1 h / 45 °C

12: pyridine / CH₂Cl₂; tetrahydrofuran

13: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -30 - -8 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; oxalyl dichloride; RhCl(PPh₃)3; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; mercury(II) oxide; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)80595-X

Reference yield:

: 120567-27-3,120707-24-6
((2S,3S,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-methanol

: 120567-34-2
Benzoic acid (2S,3R,4S)-2-acetyl-4-benzyloxymethyl-oxetan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1) Swern oxidation; 2) Et₂O, 0 degC, 2 h

2: H₂ / Pd-black / methanol / 2 h / Ambient temperature

3: TsOH / various solvent(s) / Ambient temperature

4: NaH / dimethylformamide / 2 h / 0 deg C -> room temp.

5: 83 percent / 2N HCl / dioxane / 1 h / 45 °C

6: pyridine / CH₂Cl₂; tetrahydrofuran

7: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -30 - -8 °C

With pyridine; hydrogenchloride; oxalyl dichloride; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)80595-X