(4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane

Base Information

• Chemical Name: (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane
• CAS No.: 1333237-37-8
• Molecular Formula: C₂₃H₃₂Cl₄O₅
• Molecular Weight: 530.316

Synonyms:(4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane

Chemical Property of (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane

Chemical Property:

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Technology Process of (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane

There total 9 articles about (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane 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: 83.0%

(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol (1333237-36-7) + acetone (67-64-1) → (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane (1333237-37-8)

Guidance literature:

With toluene-4-sulfonic acid; copper(II) sulfate; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/anie.201102521

Reference yield:

(3-(3-((4R,5S,6S)-6-(benzyloxymethyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,3-dichloropropyl)oxiran-2-yl)methanol → (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane (1333237-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triisopropoxytitanium(IV) chloride / hexane; benzene / 14 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid; copper(II) sulfate / 20 h / 20 °C / Inert atmosphere

With triisopropoxytitanium(IV) chloride; toluene-4-sulfonic acid; copper(II) sulfate; In hexane; benzene;

DOI:10.1002/anie.201102521

Reference yield:

(2S,3S)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-3,5,5-trichloro-2-hydroxyoctan-4-one (1333237-28-7) → (4S,5S,6R)-4-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxane (1333237-37-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate; acetic acid / acetonitrile / 1 h / 0 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 25 h / 0 - 20 °C / Inert atmosphere

3.1: tetra-n-butylammoniumfluoride trihydrate; acetic acid / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere

5.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere

5.2: 0.25 h / -78 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

7.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; tert.-butylhydroperoxide / dichloromethane; decane / 24 h / -20 °C / Molecular sieve; Inert atmosphere

8.1: magnesium chloride / ethyl acetate / 0.08 h / 80 °C / Inert atmosphere

9.1: copper(II) sulfate; toluene-4-sulfonic acid / 24 h / Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; 18-crown-6 ether; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; tetra-n-butylammoniumfluoride trihydrate; magnesium chloride; In tetrahydrofuran; decane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: |Dess-Martin Oxidation / 5.1: |Still-Gennary Z-Olefination / 5.2: |Still-Gennary Z-Olefination / 7.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1021/jacs.9b05013

upstream raw materials:

(2S,3S)-6-((4R,5S,6S)-6-((benzyloxy)methyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-3,6,6-trichlorohexane-1,2-diol

acetone

1-((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)-5-((tert-butyldiphenylsilyl)oxy)-2,2-dichloropentan-1-one

(2S,3S)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-3,5,5-trichloro-2-hydroxyoctan-4-one

Downstream raw materials:

5-((((4S,5S,6R)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxan-4-yl)methyl)thio)-1-phenyl-1H-tetrazole

5-((((4S,5S,6R)-5-chloro-2,2-dimethyl-6-((S)-1,1,4-trichloro-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)butyl)-1,3-dioxan-4-yl)methyl)sulfonyl)-1-phenyl-1H-tetrazole

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