Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester
CAS No.:211486-66-7
Molecular Formula:C₂₇H₃₂O₈S
Molecular Weight:516.612
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 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: 54.0%

: 4551-15-9
phenylthiotrimethylsilane

: 211486-65-6
Benzoic acid (2R,3R,4S,5R,6S)-5-allyloxy-2-benzyloxymethyl-4-(4-hydroxy-pentanoyloxy)-6-methoxy-tetrahydro-pyran-3-yl ester

: 211486-66-7
Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With tetra-(n-butyl)ammonium iodide; zinc(II) iodide; In 1,2-dichloro-ethane; at 60 ℃; for 6h;
DOI:10.1016/S0040-4039(98)00965-4

Reference yield:

: 131614-84-1
methyl 2-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside

: 211486-66-7
Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: DCC, DMAP / CH₂Cl₂

2: Et₃SiH, TFA / CH₂Cl₂

3: DMAP, pyridine

4: 95 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

5: 54 percent / ZnI₂, nBu₄NI / 1,2-dichloro-ethane / 6 h / 60 °C

With pyridine; triethylsilane; dmap; sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc(II) iodide; In ethanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(98)00965-4

Reference yield:

: 211486-57-6
4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-3-allyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

: 211486-66-7
Benzoic acid (2R,3R,4S,5R)-5-allyloxy-2-hydroxymethyl-4-(4-hydroxy-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: DMAP, pyridine

2: 95 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

3: 54 percent / ZnI₂, nBu₄NI / 1,2-dichloro-ethane / 6 h / 60 °C

With pyridine; dmap; sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; zinc(II) iodide; In ethanol; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(98)00965-4