(2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol

Base Information

• Chemical Name: (2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol
• CAS No.: 306726-09-0
• Molecular Formula: C₂₆H₃₆O₄Si
• Molecular Weight: 440.655
• Mol file: 306726-09-0.mol

Synonyms:(2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol

Chemical Property of (2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol

There total 2 articles about (2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-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: 90.0%

(S,S)-2,3-bis-allyloxy-butane-1,4-diol (65973-56-0) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol (306726-09-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 4h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

(2R,3R)-2,3-Bis-allyloxy-succinic acid diethyl ester (65973-54-8) → (2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol (306726-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / LAH / diethyl ether / 25 - 35 °C

2: 90 percent / NaH; Bu₄NI / tetrahydrofuran / 4 h / 0 - 25 °C

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; 1: Reduction / 2: Etherification;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

(2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol (306726-09-0) → (2R,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -40 ℃; for 4h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

upstream raw materials:

(S,S)-2,3-bis-allyloxy-butane-1,4-diol

tert-butylchlorodiphenylsilane

(2R,3R)-2,3-Bis-allyloxy-succinic acid diethyl ester

Downstream raw materials:

Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

(1S,2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butan-1-ol

(1R,2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butan-1-ol

Benzoic acid (1R,2R,3S)-2,3-bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butyl ester