(2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol

Base Information

• Chemical Name: (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol
• CAS No.: 438625-74-2
• Molecular Formula: C₄₂H₈₀O₇Si₃
• Molecular Weight: 781.349
• Mol file: 438625-74-2.mol

Synonyms:(2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol

Chemical Property of (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol

There total 4 articles about (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol 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: 94.0%

triethylsilyl chloride (994-30-9) + (2S,3S)-4-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butane-1,3-diol (438625-73-1) → (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol (438625-74-2)

Guidance literature:

With 1H-imidazole; In dichloromethane;

DOI:10.1021/ja0262683

Reference yield:

(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-2-vinyl-1,7-dioxa-spiro[5.5]undecane → (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol (438625-74-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 9-BBN / tetrahydrofuran / ultrasonic irradiation

1.2: 92 percent / H₂O₂; NaOH

2.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

3.1: TiCl₄; (-)-sparteine / CH₂Cl₂

3.2: 74 percent / LiBH₄ / methanol

4.1: 94 percent / imidazole / CH₂Cl₂

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; (-)-sparteine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;

DOI:10.1021/ja0262683

Reference yield:

[(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde (438625-72-0) → (2S,3S)-1-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-ol (438625-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TiCl₄; (-)-sparteine / CH₂Cl₂

1.2: 74 percent / LiBH₄ / methanol

2.1: 94 percent / imidazole / CH₂Cl₂

With 1H-imidazole; titanium tetrachloride; (-)-sparteine; In dichloromethane;

DOI:10.1021/ja0262683

upstream raw materials:

triethylsilyl chloride

(2S,3S)-4-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butane-1,3-diol

[(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde

2-[(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

Downstream raw materials:

(2S,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-2-((R)-3-methyl-2-methylene-4-triethylsilanyloxy-butyl)-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

(S)-1-[(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-4-triethylsilanyloxy-butan-2-one