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

Base Information

Chemical Name:(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarboxylic acid
CAS No.:114826-84-5
Molecular Formula:C₂₁H₂₃N₃O₄
Molecular Weight:381.431
Hs Code.:

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

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

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

There total 9 articles about (1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarboxylic acid 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: 93.0%

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

: 114826-84-5
(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarboxylic acid

Guidance literature:: With chromic acid; In acetone; at 0 ℃; for 10h;
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

: 114826-84-5
(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 9 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

9: 93 percent / H₂CrO₄ / acetone / 10 h / 0 °C

With sodium periodate; lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; sulfuric acid; diphenyl phosphoryl azide; chromic acid; 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; acetone; 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

: 114826-84-5
(1S,2R,3S,5S)-5-Azido-3-benzyloxy-2-benzyloxymethyl-cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 5 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

5: 93 percent / H₂CrO₄ / acetone / 10 h / 0 °C

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