(3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Base Information

• Chemical Name: (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine
• CAS No.: 221564-60-9
• Molecular Formula: C₃₄H₅₀N₂O₆Si
• Molecular Weight: 610.866

Synonyms:(3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Chemical Property of (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

Chemical Property:

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Technology Process of (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

There total 2 articles about (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine 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: 98.0%

(3S,6R,1'S,2'S,3'S)-3-[1,4-dihydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine (1018061-38-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine (221564-60-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo702601z

Reference yield: 79.0%

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose (101331-92-4) + C11H19N2O2(1-)*Li(1+) → (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine (221564-60-9)

Guidance literature:

With tin(ll) chloride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4039(99)00107-0

Reference yield: 75.0%

benzyl bromide (100-39-0) + (3S,6R,1'S,2'S,3'S)-3-[4-tert-butyldiphenylsilyloxy-1-hydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine (221564-60-9) → (3S,6R,1'S,2'S,3'S)-3-[1-benzyloxy-4-tert-butyldiphenylsilyloxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine (221564-61-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(99)00107-0

upstream raw materials:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

(3S,6R,1'S,2'S,3'S)-3-[1,4-dihydroxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

tert-butylchlorodiphenylsilane

Downstream raw materials:

(3S,6R,1'S,2'S,3'S)-3-[1-benzyloxy-4-tert-butyldiphenylsilyloxy-2,3-isopropylidenedioxybutyl]-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

4-O-benzyl-2,3-O-isopropylidene-1-deoxy-D-galactonojirimycin

ethyl (2S,3S,4R,5S)-3-benzyloxy-4,5-isopropylidenedioxypipecolate

ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

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