(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

Base Information

Chemical Name:(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde
CAS No.:114826-83-4
Molecular Formula:C₂₁H₂₃N₃O₃
Molecular Weight:365.432
Hs Code.:

Synonyms:(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

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Technology Process of (1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

There total 8 articles about (1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde 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: 92.0%

: 1-((1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentyl)-ethane-1,2-diol

: 114826-83-4
(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

Guidance literature:: With sodium periodate; In 1,4-dioxane; water; for 0.166667h; Ambient temperature;
DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

: 34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6
(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 114826-83-4
(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 1) H₂SO₄, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H⁺), 70 deg C, 15 h

2: 60 percent / NaH / dimethylformamide

3: LDA, MoOPH / tetrahydrofuran / 9 h / -78 - 20 °C

4: 91 percent / LiAlH₄ / diethyl ether / Heating

5: 80 percent / p-TsOH / benzene / Ambient temperature

6: 86 percent / (PHO)2P(O)N₃, Ph₃P, (NCO₂Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature

7: 89 percent / 80percent aq. AcOH / 7 h / Ambient temperature

8: 92 percent / NaIO₄ / dioxane; H₂O / 0.17 h / Ambient temperature

With sodium periodate; lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; sulfuric acid; diphenyl phosphoryl azide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

: 114826-80-1
1-((1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-hydroxy-cyclopentyl)-ethane-1,2-diol

: 114826-83-4
(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / p-TsOH / benzene / Ambient temperature

2: 86 percent / (PHO)2P(O)N₃, Ph₃P, (NCO₂Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature

3: 89 percent / 80percent aq. AcOH / 7 h / Ambient temperature

4: 92 percent / NaIO₄ / dioxane; H₂O / 0.17 h / Ambient temperature

With sodium periodate; diphenyl phosphoryl azide; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; water; benzene;
DOI:10.1016/S0040-4039(01)91379-6