2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 191331-64-3
• Molecular Formula: C₄₄H₄₉NO₁₅S
• Molecular Weight: 863.937
• Mol file: 191331-64-3.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl 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:

phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside (141342-83-8) + 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-fluoro-tetrahydro-pyran-2-ylmethyl ester → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-2-ylmethyl ester + 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester (191331-64-3)

Guidance literature:

With silver trifluoromethanesulfonate; tin(ll) chloride; In dichloromethane; toluene; at -20 - 20 ℃; for 4h; Yield given. Yields of byproduct given;

DOI:10.1016/S0960-894X(97)00181-9

Reference yield:

benzyl bromide (100-39-0) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester (191331-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (Bu₃Sn)2O, 2.) Bu₄NBr / 1.) toluene, reflux, 4 h, 2.) 80 deg C, 16 h

2: SnCl₂, AgOTf / CH₂Cl₂; toluene / 4 h / -20 - 20 °C

With tetrabutylammomium bromide; silver trifluoromethanesulfonate; bis(tri-n-butyltin)oxide; tin(ll) chloride; In dichloromethane; toluene;

DOI:10.1016/S0960-894X(97)00181-9

Reference yield:

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester (191331-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (Bu₃Sn)2O, 2.) Bu₄NBr / 1.) toluene, reflux, 4 h, 2.) 80 deg C, 16 h

2: SnCl₂, AgOTf / CH₂Cl₂; toluene / 4 h / -20 - 20 °C

With tetrabutylammomium bromide; silver trifluoromethanesulfonate; bis(tri-n-butyltin)oxide; tin(ll) chloride; In dichloromethane; toluene;

DOI:10.1016/S0960-894X(97)00181-9

upstream raw materials:

phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside

benzyl bromide

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Downstream raw materials:

C₇₁H₇₇NO₁₉S