Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
• CAS No.: 179072-56-1
• Molecular Formula: C₄₇H₄₈FNO₁₄
• Molecular Weight: 869.895
• Mol file: 179072-56-1.mol

Synonyms:Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 9 articles about Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-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: 90.0%

2,4,6-tri-O-benzyl-α,β-D-galactopyranosyl fluoride (179072-55-0) + phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (179072-54-9) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (179072-56-1)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; -20 deg C --> 0 deg C;

DOI:10.1016/0040-4039(96)00901-X

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (179072-56-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Bu₂SnO; 2.) CsF / 1.) MeOH, reflux, 2 h; 2.) DMF, 50 deg C, 2 d

2: 94 percent / NaH / dimethylformamide / 0.33 h / 0 °C

3: 87 percent / CAN / acetonitrile; H₂O / 0.67 h / 5 °C

4: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 73 percent / diethylaminosulfur trifluoride, NBS / CH₂Cl₂ / 1 h / -20 °C

6: Et₃N / methanol / Ambient temperature

7: 90 percent / NIS, AgOTf / CH₂Cl₂ / -20 deg C --> 0 deg C

With pyridine; N-Bromosuccinimide; N-iodo-succinimide; ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; triethylamine; cesium fluoride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00901-X

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (179072-56-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / NaH / dimethylformamide / 0.33 h / 0 °C

2: 87 percent / CAN / acetonitrile; H₂O / 0.67 h / 5 °C

3: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4: 73 percent / diethylaminosulfur trifluoride, NBS / CH₂Cl₂ / 1 h / -20 °C

5: Et₃N / methanol / Ambient temperature

6: 90 percent / NIS, AgOTf / CH₂Cl₂ / -20 deg C --> 0 deg C

With pyridine; N-Bromosuccinimide; N-iodo-succinimide; ammonium cerium(IV) nitrate; diethylamino-sulfur trifluoride; silver trifluoromethanesulfonate; sodium hydride; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00901-X

upstream raw materials:

2,4,6-tri-O-benzyl-α,β-D-galactopyranosyl fluoride

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

benzyl bromide

Downstream raw materials:

C₆₈H₇₉NO₂₀

C₇₃H₈₅NO₂₂

C₇₁H₇₃NO₂₁S