(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

Base Information

• Chemical Name: (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
• CAS No.: 1132970-10-5
• Molecular Formula: C₂₉H₄₄O₅Si
• Molecular Weight: 500.751
• Mol file: 1132970-10-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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: 92.0%

C30H42O6Si (1132970-09-2) → (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)

Guidance literature:

C₃₀H₄₂O₆Si; With lithium hydroxide; water; In tetrahydrofuran; methanol; at 20 ℃; for 0.416667h;

With ammonium chloride; In tetrahydrofuran; methanol; water;

DOI:10.1002/anie.200804645

Reference yield: 92.0%

(R)-4-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-1,3-dioxolan-2-one → (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)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.416667h;

DOI:10.1002/chem.201102797

Reference yield:

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0) → (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)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 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; water; acetonitrile;

DOI:10.1002/chem.201102797

upstream raw materials:

C₃₀H₄₂O₆Si

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

(S,Z)-1-(trityloxy)pent-3-en-2-ol

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

Downstream raw materials:

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

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

(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-hydroxy-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

Refernces

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