(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol
CAS No.:896436-07-0
Molecular Formula:C₂₁H₂₆O₅S
Molecular Weight:390.5
Hs Code.:

Synonyms:(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

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Chemical Property of (2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

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Technology Process of (2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

There total 1 articles about (2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-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: 82.0%

: 896436-02-5
(2R,3R,4S,5S,6R)-4-Allyloxy-3-methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

: 896436-07-0
(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Guidance literature:: (2R,3R,4S,5S,6R)-4-Allyloxy-3-methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran; With 1,4-diaza-bicyclo[2.2.2]octane; RhCl(PPh₃)3; In ethanol; water; for 1h; Heating;

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; at 20 ℃; for 2h;
DOI:10.1021/ja060408h

Reference yield:

: 896436-07-0
(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

: 4-Methoxy-benzoic acid (2S,3S,4R,5R,6R)-2-(2,2-dimethyl-propoxy)-5-methoxy-3-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

2: 77 percent / NaBH₄ / methanol / 0.5 h / 0 °C

3: DMAP; pyridine / 2 h / 20 °C

4: 96 percent / NBS / acetone; H₂O / 1 h / 20 °C

5: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0.2 h / 20 °C

6: 23 percent / SnCl₂; AgClO₄; MS 4A / diethyl ether / 1.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; diethylamino-sulfur trifluoride; silver perchlorate; sodium hydrogencarbonate; Dess-Martin periodane; tin(ll) chloride; In methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/ja060408h

Reference yield:

: 896436-07-0
(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

: 4-Methoxy-benzoic acid (2R,3S,4R,5R,6R)-2-(2,2-dimethyl-propoxy)-5-methoxy-3-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

2: 77 percent / NaBH₄ / methanol / 0.5 h / 0 °C

3: DMAP; pyridine / 2 h / 20 °C

4: 96 percent / NBS / acetone; H₂O / 1 h / 20 °C

5: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0.2 h / 20 °C

6: 69 percent / SnCl₂; AgClO₄; MS 4A / diethyl ether / 1.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; diethylamino-sulfur trifluoride; silver perchlorate; sodium hydrogencarbonate; Dess-Martin periodane; tin(ll) chloride; In methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/ja060408h