(3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

Base Information

Chemical Name:(3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate
CAS No.:1454318-46-7
Molecular Formula:C₂₀H₂₄O₆S₂
Molecular Weight:424.539
Hs Code.:

Synonyms:(3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

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Chemical Property of (3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

Chemical Property:

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Technology Process of (3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

There total 6 articles about (3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate 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: 92.0%

: 1454318-42-3
(3S,4R,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-ol

: 124-63-0
methanesulfonyl chloride

: 1454318-46-7
(3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

Guidance literature:: With pyridine; at 0 - 4 ℃; for 24.5h; Inert atmosphere;
DOI:10.1016/j.tet.2013.07.093

Reference yield:

: 1454318-37-6
(3S,4R,5R)-5-(benzyloxymethyl)-4-(p-tolylthio)-tetrahydrofuran-3-ol

: 1454318-46-7
(3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere

2: pyridine / 24.5 h / 0 - 4 °C / Inert atmosphere

With pyridine; sodium periodate; In methanol; water;
DOI:10.1016/j.tet.2013.07.093

Reference yield:

: 20535-09-5
2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle

: 1454318-46-7
(3S,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N,N',N'-tetramethylguanidine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

1.2: 5 h / 100 °C / Inert atmosphere

2.1: trifluoroacetic acid / water / 10 h / 20 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C / Inert atmosphere

3.1: p-toluenesulfonyl chloride; pyridine / toluene / 72.5 h / 0 - 4 °C / Inert atmosphere

4.1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere

5.1: pyridine / 24.5 h / 0 - 4 °C / Inert atmosphere

With pyridine; sodium periodate; p-toluenesulfonyl chloride; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In methanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2013.07.093