(2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 188424-09-1
• Molecular Formula: C₁₈H₂₅NO₁₁
• Molecular Weight: 431.397
• Mol file: 188424-09-1.mol

Synonyms:

Chemical Property of (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol 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:

(2S,3R,4R,5R,6S)-2-Methyl-6-[(2R,3aR,4S,6S,7R,7aR)-4-methyl-6-(4-nitro-phenoxy)-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-3,4,5-triol → (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol (188424-09-1)

Guidance literature:

With acetic acid; at 70 ℃; for 0.333333h; Yield given;

DOI:10.1016/S0008-6215(96)00255-8

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranose (28915-80-2,40591-53-5,40591-54-6,40591-55-7,120449-19-6,120449-20-9,143332-42-7,148081-39-4,151413-57-9,151413-58-0) → (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol (188424-09-1)

Guidance literature:

Multi-step reaction with 4 steps

1: DBU / CH₂Cl₂ / 0.33 h

2: 94.2 percent / Me₃SiOTf / CH₂Cl₂ / 0.33 h / -40 °C

3: NaOMe / methanol / Ambient temperature

4: aq. HOAc / 0.33 h / 70 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(96)00255-8

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → (2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-4,5-Dihydroxy-6-methyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol (188424-09-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94.2 percent / Me₃SiOTf / CH₂Cl₂ / 0.33 h / -40 °C

2: NaOMe / methanol / Ambient temperature

3: aq. HOAc / 0.33 h / 70 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(96)00255-8

upstream raw materials:

2,3,4-tri-O-acetyl-L-rhamnopyranose

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-[(2R,3aR,4S,6S,7R,7aR)-4-methyl-6-(4-nitro-phenoxy)-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-3-yl ester

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide