4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
CAS No.:263358-68-5
Molecular Formula:C₆₀H₆₁NO₁₃S
Molecular Weight:1036.21
Hs Code.:

4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Synonyms:4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of 4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of 4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 5 articles about 4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-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: 91.0%

: 263358-62-9
ethyl 3-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 263358-65-2
3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl phenylcarbonate

: 263358-68-5
4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With calcium sulfate; tert-butyl isocyanide; trityl tetrakis(pentafluorophenyl)borate; In dichloromethane; at -20 ℃; for 6h;
DOI:10.1246/cl.2000.122

Reference yield:

: 20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1
3,4,6-tri-O-benzyl-D-glucopyranose

: 263358-68-5
4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / DMAP / pyridine / 0 - 20 °C

2: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

3: 90 percent / aq. TfOH; n-Bu₄NIO₄ / acetonitrile / 0 °C

4: 48 percent / Et₃N / CH₂Cl₂ / 20 °C

5: 91 percent / trityl tetrakis(pentafluorophenyl)borate; Drierite; pivalonitrile / CH₂Cl₂ / 6 h / -20 °C

With dmap; calcium sulfate; tert-butyl isocyanide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutylammonium periodite; triethylamine; trityl tetrakis(pentafluorophenyl)borate; In pyridine; dichloromethane; acetonitrile; 1: Acylation / 2: Alkylation / 3: Hydrolysis / 4: Acylation / 5: Etherification;
DOI:10.1246/cl.2000.122

Reference yield:

: 4-Methyl-benzoic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl ester

: 263358-68-5
4-Methyl-benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4-acetoxy-3-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 48 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 91 percent / trityl tetrakis(pentafluorophenyl)borate; Drierite; pivalonitrile / CH₂Cl₂ / 6 h / -20 °C

With calcium sulfate; tert-butyl isocyanide; triethylamine; trityl tetrakis(pentafluorophenyl)borate; In dichloromethane; 1: Acylation / 2: Etherification;
DOI:10.1246/cl.2000.122