(1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol

Base Information

• Chemical Name: (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol
• CAS No.: 780789-23-3
• Molecular Formula: C₂₀H₃₁N₃O₉
• Molecular Weight: 457.481

Synonyms:(1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol

Chemical Property of (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol

Chemical Property:

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Technology Process of (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol

There total 13 articles about (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol 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: 78.0%

(1S,2S,3R,4R,5S)-4-(4-Methoxy-benzyloxy)-2,3-bis-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexane (780789-22-2) → (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol (780789-23-3)

Guidance literature:

With sodium azide; ammonium chloride; In ethylene glycol; N,N-dimethyl-formamide; at 120 ℃;

DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

cis-3-[[(4-methoxyphenyl)methoxy]methyl]-oxiranemethanol → (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol (780789-23-3)

Guidance literature:

Multi-step reaction with 13 steps

1: IBX; pyridine / dimethylsulfoxide / 45 °C

2: KHMDS / toluene; tetrahydrofuran / -20 - 20 °C

3: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

4: 88 percent / imidazole / dimethylformamide / 20 °C

5: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6: 51 percent / 1,2-dimethoxy-ethane / 0 - 20 °C

7: p-TsOH / -78 - 0 °C

8: TBAF / tetrahydrofuran / 20 °C

9: 73 percent / L-(+)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / -20 °C

10: 87 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

11: 85 percent / NaOAc / PdCl₂ / acetic acid; H₂O / 20 °C

12: 86 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

13: 78 percent / NaN₃; NH₄Cl / dimethylformamide; ethane-1,2-diol / 120 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium acetate; potassium hexamethylsilazane; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dichloride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethylene glycol; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 2: Wittig reaction / 9: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

(2S,3S)-3-(4-Methoxy-benzyloxymethyl)-oxirane-2-carbaldehyde → (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol (780789-23-3)

Guidance literature:

Multi-step reaction with 12 steps

1: KHMDS / toluene; tetrahydrofuran / -20 - 20 °C

2: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

3: 88 percent / imidazole / dimethylformamide / 20 °C

4: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5: 51 percent / 1,2-dimethoxy-ethane / 0 - 20 °C

6: p-TsOH / -78 - 0 °C

7: TBAF / tetrahydrofuran / 20 °C

8: 73 percent / L-(+)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / -20 °C

9: 87 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

10: 85 percent / NaOAc / PdCl₂ / acetic acid; H₂O / 20 °C

11: 86 percent / iPr₂NEt / CH₂Cl₂ / 20 °C

12: 78 percent / NaN₃; NH₄Cl / dimethylformamide; ethane-1,2-diol / 120 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium acetate; potassium hexamethylsilazane; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium dichloride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethylene glycol; acetic acid; N,N-dimethyl-formamide; toluene; 1: Wittig reaction / 8: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2004.07.087

upstream raw materials:

(1S,2S,3R,4R,5S)-4-(4-Methoxy-benzyloxy)-2,3-bis-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexane

(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

tert-Butyl-[(1S,4S,5R)-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hex-2-en-2-ylmethoxy]-dimethyl-silane

(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

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