S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

Base Information

Chemical Name:S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol
CAS No.:274905-44-1
Molecular Formula:C₂₁H₂₆O₄S
Molecular Weight:374.501
Hs Code.:

Synonyms:S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

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Chemical Property of S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

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Technology Process of S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

There total 3 articles about S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol 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: 70.0%

: 100-39-0
benzyl bromide

: 274905-41-8
S(R)-1-deoxy-1-(p-tolylsulfinyl)-3,4-O-isopropylidene-D-erythritol

: 274905-44-1
S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

Guidance literature:: S(R)-1-deoxy-1-(p-tolylsulfinyl)-3,4-O-isopropylidene-D-erythritol; With sodium hydride; In tetrahydrofuran; for 0.5h; Heating;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 20h;
DOI:10.1016/S0957-4166(00)00005-7

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 274905-44-1
S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 70 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / Heating

2.2: 70 percent / tBuNI / tetrahydrofuran / 20 h / 20 °C

With sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1.1: Metallation / 1.2: Addition / 2.1: Metallation / 2.2: Alkylation;
DOI:10.1016/S0957-4166(00)00005-7

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 274905-44-1
S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 70 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / Heating

2.2: 70 percent / tBuNI / tetrahydrofuran / 20 h / 20 °C

With sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1.1: Metallation / 1.2: Addition / 2.1: Metallation / 2.2: Alkylation;
DOI:10.1016/S0957-4166(00)00005-7