(2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran

Base Information

• Chemical Name: (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran
• CAS No.: 870096-05-2
• Molecular Formula: C₁₄H₂₀O₄S
• Molecular Weight: 284.376
• Mol file: 870096-05-2.mol

Synonyms:(2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran

Chemical Property of (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran

There total 3 articles about (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran 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: 93.0%

(2S,3R,4S,5R)-2-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (52544-91-9,52544-92-0,62774-34-9,98461-49-5,107961-02-4,107961-33-1,110221-83-5) + methyl iodide (74-88-4) → (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran (870096-05-2)

Guidance literature:

(2S,3R,4S,5R)-2-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate; With sodium methylate; In methanol; at 20 ℃; for 2h;

methyl iodide; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 15h;

DOI:10.1002/anie.201506618

Reference yield:

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran (870096-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic anhydride / 4 h / Reflux

2.1: molybdenum(VI) oxychloride / dichloromethane / 12 h / 20 °C

3.1: sodium methylate / methanol / 2 h / 20 °C

3.2: 15 h / 0 - 20 °C

With molybdenum(VI) oxychloride; sodium methylate; In methanol; dichloromethane; acetic anhydride;

DOI:10.1002/anie.201506618

Reference yield:

tetra-O-acetyl-β-D-xylopyranose (4049-33-6) → (2S,3R,4S,5R)-3,4,5-trimethoxy-2-(phenylthio)tetrahydro-2H-pyran (870096-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: molybdenum(VI) oxychloride / dichloromethane / 12 h / 20 °C

2.1: sodium methylate / methanol / 2 h / 20 °C

2.2: 15 h / 0 - 20 °C

With molybdenum(VI) oxychloride; sodium methylate; In methanol; dichloromethane;

DOI:10.1002/anie.201506618

upstream raw materials:

D-Xylose

tetra-O-acetyl-β-D-xylopyranose

(2S,3R,4S,5R)-2-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

methyl iodide

Downstream raw materials:

C₂₆H₄₀O₉

C₂₆H₄₀O₉

C₂₅H₃₈O₉

C₂₅H₃₈O₉