(2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane

Base Information

• Chemical Name: (2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane
• CAS No.: 120567-31-9
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.419
• Mol file: 120567-31-9.mol

Synonyms:

Chemical Property of (2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane

There total 23 articles about (2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane 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: 87.0%

1-((3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-ethanol (120567-30-8,120663-08-3,127912-20-3,133005-78-4) → (3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane (120567-31-9,120567-37-5)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)94349-1

Reference yield:

(S)-1-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-ethanol (120567-30-8,120663-08-3,127912-20-3,133005-78-4) → (2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane (120567-31-9)

Guidance literature:

With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/S0040-4020(01)90066-3

Reference yield:

3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose (69827-91-4) → (2S,3R,4S)-3,4-Bis(benzyloxymethyl)-2-acetyloxetane (120567-31-9)

Guidance literature:

Multi-step reaction with 8 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: 50 percent / Swern oxidation

With 1,4-diaza-bicyclo[2.2.2]octane; RhCl(PPh₃)3; tetrabutyl ammonium fluoride; sodium hydride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)80595-X

upstream raw materials:

1-((3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-ethanol

benzaldehyde dimethyl acetal

(2S,3R)-1-Benzyloxy-3-benzyloxy-4,5-trans-epoxyhexan-2-ol

(Z)-(2S,3R)-1-Benzyloxy-3-benzyloxymethyl-4-hexen-2-ol

Downstream raw materials:

C₂₁H₂₀O₆

C₂₁H₂₀O₇

1-O-Acetyl-2-deoxy-2-hydroxymethyl-D-erythrooxtanose dibenzoate