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

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 202865-04-1
• Molecular Formula: C₅₄H₅₃Cl₂NO₁₆
• Molecular Weight: 1042.92
• Mol file: 202865-04-1.mol

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

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

There total 14 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-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:

4,5-dichlorophthalic anhydride (942-06-3) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (202865-04-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Et₃N, 2.) Ac₂O, pyridine / 1) 1,2-dichloroethane, 50-60 deg C, 2 h; 2) rt, 24 h

2: 87 percent / TMSOTf / 1,2-dichloro-ethane / 42 h

3: 25 g / NaOMe / methanol; CH₂Cl₂ / 4 h / 0 °C

4: 74 percent / camphorsulphonic acid / dimethylformamide / 60 h / Ambient temperature

5: 4 Angstroem molecular sieves, NaH / dimethylformamide / 28 h / 6 °C

6: 4 Angstroem molecular sieves, sodium cyanoborohydride, aq. HCl / tetrahydrofuran / 7 h / Ambient temperature

7: 1.) 4 Angstroem molecular sieves, N-iodosuccinimide, 2.) TfOH / 1) CH₂Cl₂, 0 deg C, 20 min; 2) CH₂Cl₂, 0 deg C, 1 h

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic anhydride; sodium hydride; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10377-5

Reference yield:

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (202865-04-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Et₃N, 2.) Ac₂O, pyridine / 1) 1,2-dichloroethane, 50-60 deg C, 2 h; 2) rt, 24 h

2: 87 percent / TMSOTf / 1,2-dichloro-ethane / 42 h

3: 25 g / NaOMe / methanol; CH₂Cl₂ / 4 h / 0 °C

4: 74 percent / camphorsulphonic acid / dimethylformamide / 60 h / Ambient temperature

5: 4 Angstroem molecular sieves, NaH / dimethylformamide / 28 h / 6 °C

6: 4 Angstroem molecular sieves, sodium cyanoborohydride, aq. HCl / tetrahydrofuran / 7 h / Ambient temperature

7: 1.) 4 Angstroem molecular sieves, N-iodosuccinimide, 2.) TfOH / 1) CH₂Cl₂, 0 deg C, 20 min; 2) CH₂Cl₂, 0 deg C, 1 h

With pyridine; hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic anhydride; sodium hydride; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10377-5

Reference yield:

1,2,3,4-tetra-O-acetyl- 6-O-benzyl-α/β-D-galactopyranoside (196942-01-5) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (202865-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / 4 Angstroem molecular sieves, BF₃*OEt₂ / CH₂Cl₂ / 44 h / Ambient temperature

2: 1.) 4 Angstroem molecular sieves, N-iodosuccinimide, 2.) TfOH / 1) CH₂Cl₂, 0 deg C, 20 min; 2) CH₂Cl₂, 0 deg C, 1 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0040-4020(97)10377-5

upstream raw materials:

acetic anhydride

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-5,6-dichloro-isoindole-1,3-dione

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate

Downstream raw materials:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-5,6-dichloro-isoindole-1,3-dione