(2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol

Base Information

• Chemical Name: (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol
• CAS No.: 143396-26-3
• Molecular Formula: C₂₃H₃₆O₄Si
• Molecular Weight: 404.622
• Mol file: 143396-26-3.mol

Synonyms:(2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol

Chemical Property of (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol

There total 2 articles about (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-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: 93.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R,4R)-1-benzyloxy-2,3-O-isopropylidenehept-6-yne-2,3,4-triol (143396-25-2) → (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol (143396-26-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1039/P19920002705

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol (143396-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Zn-dust / dimethylformamide; diethyl ether

2: 93 percent / imidazole

With 1H-imidazole; zinc; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74811-8

Reference yield:

(2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol (143396-26-3) → (9Z,15Z)-(11R,12S,13R)-11,12-Dihydroxy-13-(toluene-4-sulfonyloxy)-octadeca-9,15-dienoic acid methyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: 1) n-BuLi, HMPA / 1) THF

2: 98 percent / H₂, quinoline / Pd-Pb-CaCO₃

3: 96 percent / Li, liq. NH₃

4: 1) DMSO, (COCl)2, 2) NEt₃

5: t-BuOK / tetrahydrofuran

6: 95 percent / n-Bu₄NF

7: pyridine

8: PTS / H₂O

With pyridine; quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; hydrogen; pyridinium p-toluenesulfonate; lithium; dimethyl sulfoxide; triethylamine; Pd-Pb-CaCO₃ (Lindlar catalyst); In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)74811-8

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R,4R)-1-benzyloxy-2,3-O-isopropylidenehept-6-yne-2,3,4-triol

4-O-benzyl-2,3-O-isopropylidene-D-threose

Downstream raw materials:

(2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenedodec-6-yne-2,3-diol

(Z)-10-{(4R,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester

[(Z)-(R)-1-((4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-3-enyloxy]-tert-butyl-dimethyl-silane

(2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenedodec-6-ene-2,3-diol