(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

Base Information

• Chemical Name: (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
• CAS No.: 438625-73-1
• Molecular Formula: C₃₆H₆₆O₇Si₂
• Molecular Weight: 667.087
• Mol file: 438625-73-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 74.0%

N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione (145588-95-0,334968-78-4) + [(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)-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)

Guidance literature:

N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione; [(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; With titanium tetrachloride; (-)-sparteine; In dichloromethane;

With lithium borohydride; In methanol; Further stages.;

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)-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)

Guidance literature:

Multi-step reaction with 3 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

With 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:

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 (438625-91-3) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

2.1: TiCl₄; (-)-sparteine / CH₂Cl₂

2.2: 74 percent / LiBH₄ / methanol

With oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; (-)-sparteine; In dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/ja0262683

upstream raw materials:

N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione

[(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,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

(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

(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