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

Base Information

• Chemical Name: (1S,2S,3R,4R,5S)-4-(4-Methoxy-benzyloxy)-2,3-bis-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexane
• CAS No.: 780789-22-2
• Molecular Formula: C₂₀H₃₀O₉
• Molecular Weight: 414.453

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 36 articles about (1S,2S,3R,4R,5S)-4-(4-Methoxy-benzyloxy)-2,3-bis-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexane 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: 86.0%

chloromethyl methyl ether (107-30-2) + (1R,2S,3S,4R,5S)-4-(4-Methoxy-benzyloxy)-3-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexan-2-ol (780789-26-6) → (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)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

cis-3-[[(4-methoxyphenyl)methoxy]methyl]-oxiranemethanol → (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)

Guidance literature:

Multi-step reaction with 12 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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium acetate; potassium hexamethylsilazane; 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; 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 → (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)

Guidance literature:

Multi-step reaction with 11 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

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

DOI:10.1016/j.tetlet.2004.07.087

upstream raw materials:

chloromethyl methyl ether

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

(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

Downstream raw materials:

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

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