(2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

Base Information

Chemical Name:(2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol
CAS No.:156479-43-5
Molecular Formula:C₂₃H₃₀O₆S
Molecular Weight:434.554
Hs Code.:

Synonyms:(2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

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Technology Process of (2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

There total 3 articles about (2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-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: 84.0%

: 98-59-9
p-toluenesulfonyl chloride

: 156479-42-4
(2R,3S,4S)-5-benzyloxymethoxy-4-methyl-2-vinylpentane-1,3-diol

: 156479-43-5
(2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

Guidance literature:: With pyridine; at 10 ℃; for 28h;
DOI:10.1248/cpb.41.2044

Reference yield:

: (E)-(R)-5-Benzyloxymethoxy-4-methyl-pent-2-en-1-ol

: 156479-43-5
(2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.)titanium tetra-isopropoxide, molecular sieves 3A, diethyl (+)-tartrate, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) CH₂Cl₂, 2,2,4-trimethylpentane, -20 deg C, 12 h

2: 1.) CuI / 1.) THF, Et₂O, from -30 deg C to -20 deg C, 10 min, 2.) THF, Et₂O, -20 deg, 1 h

3: 84 percent / pyridine / 28 h / 10 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2R,3R)-tartrate; 3 A molecular sieve;
DOI:10.1248/cpb.41.2044

Reference yield:

: 156557-41-4
(4S)-5-benzyloxymethyloxy-2,3-epoxy-4-methylpentan-1-ol

: 156479-43-5
(2S,3S,4R)-1-benzyloxymethoxy-2-methyl-4-(4-methylphenylsulfonyloxymethyl)hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) CuI / 1.) THF, Et₂O, from -30 deg C to -20 deg C, 10 min, 2.) THF, Et₂O, -20 deg, 1 h

2: 84 percent / pyridine / 28 h / 10 °C

With pyridine; copper(l) iodide;
DOI:10.1248/cpb.41.2044