Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 139302-31-1
• Molecular Formula: C₄₃H₄₇NO₁₅
• Molecular Weight: 817.844
• Mol file: 139302-31-1.mol

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-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: 61.0%

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (107823-72-3) + methyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside (130282-60-9) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (139302-31-1) + Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-6-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (139302-29-7)

Guidance literature:

With methyl trifluoromethanesulfonate; In toluene; at -15 ℃;

DOI:10.1016/0008-6215(94)00264-9

Reference yield: 4.0%

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (162740-42-3) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (139302-31-1) + Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-5-benzyloxy-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; In tetrahydrofuran;

DOI:10.1016/0008-6215(95)00112-7

Reference yield:

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (120142-50-9) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (139302-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / MeOTf / CH₂Cl₂ / Ambient temperature

2: 89 percent / BH₃*NMe₃, TMSOTf / tetrahydrofuran

With trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0008-6215(95)00112-7

upstream raw materials:

allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

methyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

C₇₀H₇₅NO₁₉