5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

Base Information

• Chemical Name: 5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol
• CAS No.: 605668-77-7
• Molecular Formula: C₁₉H₂₃BrO₄S
• Molecular Weight: 427.359

Synonyms:5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

Chemical Property of 5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of 5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

There total 2 articles about 5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-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: 88.0%

5-benzyloxy-1-(SR)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol (110426-22-7) → 5-benzyloxy-4-bromo-1-(SS)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol (605668-77-7)

Guidance literature:

With N-Bromosuccinimide; water; In toluene; at 20 ℃; for 0.25h;

DOI:10.1016/S0957-4166(03)00427-0

Reference yield:

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one (110426-21-6) → 5-benzyloxy-4-bromo-1-(SS)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol (605668-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / DIBAH; ZnCl₂ / tetrahydrofuran / 0.5 h / -78 °C

2: 88 percent / NBS; H₂O / toluene / 0.25 h / 20 °C

With N-Bromosuccinimide; water; diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(03)01650-2

Reference yield: 90.0%

5-benzyloxy-4-bromo-1-(SS)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol (605668-77-7) → (R)-1-((2R,3R)-3-Benzyloxymethyl-oxiranyl)-2-((S)-toluene-4-sulfinyl)-ethanol (900792-39-4)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1016/j.tetlet.2006.05.043

upstream raw materials:

5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one

Downstream raw materials:

4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane

(R)-1-((2R,3R)-3-Benzyloxymethyl-oxiranyl)-2-((S)-toluene-4-sulfinyl)-ethanol

(S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol

Benzoic acid (1S,2R,3R)-1-benzyloxymethyl-2,3-dihydroxy-4-((S)-toluene-4-sulfinyl)-butyl ester

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