(4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde

Base Information

• Chemical Name: (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde
• CAS No.: 1132969-86-8
• Molecular Formula: C₂₈H₄₀O₄Si
• Molecular Weight: 468.709
• Mol file: 1132969-86-8.mol

Synonyms:(4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde

Chemical Property of (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde

There total 13 articles about (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde 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%

(R)-1-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethane-1,2-diol (1132970-10-5) → (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde (1132969-86-8)

Guidance literature:

With NaIO₄ absorbed on silica gel; In chloroform; at 20 ℃; for 0.466667h; Inert atmosphere;

DOI:10.1002/anie.200804645

Reference yield:

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0) → (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde (1132969-86-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

2.2: 0.42 h / 0 °C

3.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

4.1: dichloromethane / -78 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

7.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

8.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

9.1: toluene-4-sulfonic acid / 0.33 h / 20 °C / Inert atmosphere

10.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.42 h / 20 °C

11.1: sodium periodate / chloroform / 0.47 h / 20 °C / Inert atmosphere

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; lithium borohydride; hydroxylamine hydrochloride; hydrogen; boric acid; toluene-4-sulfonic acid; acetic acid; potassium bromide; lithium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; acetonitrile;

DOI:10.1002/chem.201102797

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde (1132969-86-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 44 h / 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

3.2: 0.42 h / 0 °C

4.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

5.1: dichloromethane / -78 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

7.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

8.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

9.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / 0.33 h / 20 °C / Inert atmosphere

11.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.42 h / 20 °C

12.1: sodium periodate / chloroform / 0.47 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; lithium borohydride; hydroxylamine hydrochloride; hydrogen; boric acid; toluene-4-sulfonic acid; acetic acid; potassium bromide; lithium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.201102797

upstream raw materials:

(R)-1-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethane-1,2-diol

(2S,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanal oxime

(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)-2-(trityloxy)ethanol

(R)-1-((4S,5R)-3-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-4-methyl-4,5-dihydroisoxazol-5-yl)ethane-1,2-diol

Downstream raw materials:

methyl (2Z,4E,6R,7S,8S,10E,14S)-14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-14-hydroxy-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilyloxy)tetradeca-2,4,10-trien-12-ynoate

Refernces

• 1、 Kleinbeck, Florian,Carreira, Erick M.. "Total synthesis of bafilomycin A1". supporting information; experimental part. p. 578 - 581. Retrieved 2009/04/14.