(2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol
CAS No.:445299-14-9
Molecular Formula:C₁₉H₂₂O₅S
Molecular Weight:362.447
Hs Code.:

Synonyms:(2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

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Chemical Property of (2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

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Technology Process of (2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

There total 3 articles about (2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-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: 57.0%

: 100-39-0
benzyl bromide

: 1053626-36-0
phenyl 2-thio-β-D-fructopyranoside

: 445299-14-9
(2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Guidance literature:: phenyl 2-thio-β-D-fructopyranoside; With 4 A molecular sieve; di(n-butyl)tin oxide; In acetonitrile; for 5h; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In acetonitrile; for 17h; Heating;
DOI:10.1016/S0040-4020(02)00233-8

Reference yield:

: 108-98-5
thiophenol

: 445299-14-9
(2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 14 h / 20 °C

1.2: 41 percent / Et₃N; H₂O / methanol / 16 h / 40 °C

2.1: Bu₂SnO; 4 Angstroem molecular sieves / acetonitrile / 5 h / Heating

2.2: 57 percent / tertrabutylammonium iodide / acetonitrile / 17 h / Heating

With 4 A molecular sieve; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(02)00233-8

Reference yield:

: 99042-47-4
2'-chloroethyl 1,3,4,5-tetra-O-acetyl-β-D-fructopyranoside

: 445299-14-9
(2S,3S,4R,5R)-4-Benzyloxy-2-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 14 h / 20 °C

1.2: 41 percent / Et₃N; H₂O / methanol / 16 h / 40 °C

2.1: Bu₂SnO; 4 Angstroem molecular sieves / acetonitrile / 5 h / Heating

2.2: 57 percent / tertrabutylammonium iodide / acetonitrile / 17 h / Heating

With 4 A molecular sieve; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(02)00233-8