(1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Base Information

• Chemical Name: (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol
• CAS No.: 404893-43-2
• Molecular Formula: C₄₄H₄₈O₉
• Molecular Weight: 720.86

Synonyms:(1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Chemical Property of (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

There total 13 articles about (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol 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: 100.0%

Benzoic acid (1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester (404893-42-1) → (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol (404893-43-2)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(01)01946-3

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol (404893-43-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 73 percent / NaIO₄; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

2: 59 percent / CuBr-Me₂S / tetrahydrofuran; various solvent(s) / 2 h / -40 - 20 °C

3: 95 percent / NaH / dimethylformamide

4: 92 percent / 80 percent AcOH / 48 h / 70 °C

5: 68 percent / n-BuLi / diethyl ether / 20 °C

6: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 20 °C

7: 92 percent / NaH / dimethylformamide

8: 98 percent / OsO₄; quinuclidine; NMO / CH₂Cl₂ / 20 °C

9: DMAP / pyridine

10: 30 percent / diisopropylethylamine; n-Bu₄NBr / CH₂Cl₂ / 48 h / 70 °C

11: 100 percent / K₂CO₃ / methanol / 4 h / 20 °C

With Quinuclidine; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrabutylammomium bromide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Wittig methylenation;

DOI:10.1016/S0040-4039(01)01946-3

Reference yield:

benzyl bromide (100-39-0) → (1S,2S,3R,4S,5R,6S)-2,4-Bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol (404893-43-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 89 percent / NaH / dimethylformamide

2: 95 percent / 60 percent aq. AcOH / 20 °C

3: 73 percent / NaIO₄; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

4: 59 percent / CuBr-Me₂S / tetrahydrofuran; various solvent(s) / 2 h / -40 - 20 °C

5: 95 percent / NaH / dimethylformamide

6: 92 percent / 80 percent AcOH / 48 h / 70 °C

7: 68 percent / n-BuLi / diethyl ether / 20 °C

8: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 20 °C

9: 92 percent / NaH / dimethylformamide

10: 98 percent / OsO₄; quinuclidine; NMO / CH₂Cl₂ / 20 °C

11: DMAP / pyridine

12: 30 percent / diisopropylethylamine; n-Bu₄NBr / CH₂Cl₂ / 48 h / 70 °C

13: 100 percent / K₂CO₃ / methanol / 4 h / 20 °C

With Quinuclidine; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrabutylammomium bromide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 7: Wittig methylenation;

DOI:10.1016/S0040-4039(01)01946-3

upstream raw materials:

Benzoic acid (1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexyl ester

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester

Octadecanoic acid (R)-3-{benzyloxy-[(1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryloxy}-2-butyryloxy-propyl ester

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