methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside
• CAS No.: 110889-33-3
• Molecular Formula: C₂₆H₃₈O₁₂S
• Molecular Weight: 574.647

Synonyms:methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside

Chemical Property of methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside

There total 8 articles about methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside 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: 20.0%

methyl 11-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,21-O-isopropylidene-6-O-pivaloyl-α-D-glucopyranoside (110889-32-2) + p-toluenesulfonyl chloride (98-59-9) → methyl 11-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,21-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside (110889-33-3)

Guidance literature:

With dmap; In pyridine; dichloromethane; at 40 ℃; for 168h;

DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

methyl 4,6-O-benzylidene-3-C-<(Z)-2-hydroxyethylidene>-2,21-O-isopropylidene-α-D-ribo-hexopyranoside (110889-27-5) → methyl 11-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,21-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside (110889-33-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 62 percent / osmium tetraoxide, 4-methylmorpholine N-oxide, water / 2-methyl-propan-2-ol; tetrahydrofuran / Ambient temperature

2: dimethyl sulfoxide, oxalyl chloride, triethylamine / 2-methyl-propan-2-ol; CH₂Cl₂; H₂O / 1 h, room temperature

3: sodium borohydride / methanol / 1 h

4: pyridine

5: hydrogen, acetic acid / palladium hydroxide on charcoal / ethanol / 44 h / Ambient temperature

6: 87 percent / pyridine / 24 h / 60 °C

7: 20 percent / 4-dimethylaminopyridine / pyridine; CH₂Cl₂ / 168 h / 40 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; oxalyl dichloride; water; hydrogen; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0008-6215(00)90006-5

Reference yield:

Acetic acid (4aR,6S,6aR,11S,11aS,11bR)-11a-hydroxy-6-methoxy-8,8-dimethyl-2-phenyl-octahydro-1,3,5,7,9-pentaoxa-cyclohepta[a]naphthalen-11-yl ester (110889-30-0) → methyl 11-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,21-O-isopropylidene-6-O-pivaloyl-4-O-p-tolylsulfonyl-α-D-glucopyranoside (110889-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen, acetic acid / palladium hydroxide on charcoal / ethanol / 44 h / Ambient temperature

2: 87 percent / pyridine / 24 h / 60 °C

3: 20 percent / 4-dimethylaminopyridine / pyridine; CH₂Cl₂ / 168 h / 40 °C

With pyridine; dmap; hydrogen; acetic acid; palladium hydroxide - carbon; In pyridine; ethanol; dichloromethane;

DOI:10.1016/S0008-6215(00)90006-5

upstream raw materials:

methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-6-O-pivaloyl-α-D-glucopyranoside

p-toluenesulfonyl chloride

methyl 1¹-O-acetyl-3-C-<(S)-1,2-dihydroxyethyl>-2,2¹-O-isopropylidene-α-D-glucopyranoside

methyl 4,6-O-benzylidene-3-C-<(Z)-2-hydroxyethylidene>-2,2¹-O-isopropylidene-α-D-ribo-hexopyranoside

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