(2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al

Base Information

• Chemical Name: (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al
• CAS No.: 1227373-79-6
• Molecular Formula: C₄₂H₈₄O₇Si₄
• Molecular Weight: 813.467
• Mol file: 1227373-79-6.mol

Synonyms:(2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al

Chemical Property of (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al

There total 13 articles about (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al 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: 93.0%

(2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-ol (1227374-12-0) → (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al (1227373-79-6)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0029-1219376

Reference yield:

2-{(2S)-2-[(tert-butyldimethylsilyl)oxy]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-propyl}-1,3-dithiane (1196989-22-6) → (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al (1227373-79-6)

Guidance literature:

Multi-step reaction with 8 steps

1: acetyl chloride / methanol / Inert atmosphere

2: 2,6-dimethylpyridine / Inert atmosphere

3: tert.-butyl lithium / tetrahydrofuran / Inert atmosphere

4: 2,6-dimethylpyridine; mercury(II) perchlorate trihydrate / Inert atmosphere

5: tetramethylammonium triacetoxyborohydride / Inert atmosphere

6: 2,6-dimethylpyridine / Inert atmosphere

7: pyridine hydrogenfluoride / Inert atmosphere

8: Dess-Martin periodane / Inert atmosphere

With 2,6-dimethylpyridine; mercury(II) perchlorate trihydrate; tetramethylammonium triacetoxyborohydride; tert.-butyl lithium; Dess-Martin periodane; pyridine hydrogenfluoride; acetyl chloride; In tetrahydrofuran; methanol;

DOI:10.1021/ol200735r

Reference yield:

C15H32O3S2Si → (2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-al (1227373-79-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 2,6-dimethylpyridine / Inert atmosphere

2: tert.-butyl lithium / tetrahydrofuran / Inert atmosphere

3: 2,6-dimethylpyridine; mercury(II) perchlorate trihydrate / Inert atmosphere

4: tetramethylammonium triacetoxyborohydride / Inert atmosphere

5: 2,6-dimethylpyridine / Inert atmosphere

6: pyridine hydrogenfluoride / Inert atmosphere

7: Dess-Martin periodane / Inert atmosphere

With 2,6-dimethylpyridine; mercury(II) perchlorate trihydrate; tetramethylammonium triacetoxyborohydride; tert.-butyl lithium; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1021/ol200735r

upstream raw materials:

(2S,4R,6S,8R)-10-(4-methoxybenzyloxy)-2,4,6,8-tetrakis(tert-butyldimethylsilyloxy)decan-1-ol

(2S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(1,3-dithian-2-yl)propan-2-ol

2-{(2S)-2-[(tert-butyldimethylsilyl)oxy]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-propyl}-1,3-dithiane

2-((2S,4S)-2,4,5-tris(tert-butyldimethylsilyloxy)pentyl)-1,3-dithiane

Downstream raw materials:

C₇₄H₁₄₇NO₁₂Si₆