2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione

Base Information

• Chemical Name: 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione
• CAS No.: 155793-68-3
• Molecular Formula: C₃₆H₄₃NO₁₀
• Molecular Weight: 649.738
• Mol file: 155793-68-3.mol

Synonyms:2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione

Chemical Property of 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione

There total 9 articles about 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione 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: 76.0%

benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside (155681-03-1) + [(3aR,4S,6S,7R,7aR)-6-tert-Butoxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl]-triphenyl-phosphonium; iodide → 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione (155793-68-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - -10 ℃; for 1h;

DOI:10.1016/S0008-6215(97)00018-9

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranosyl bromide (110455-06-6) → 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione (155793-68-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 7.4 g / AgOTf, sym-collidine / CH₂Cl₂ / 2 h / 0 °C

2: 5.5 g / MeONa / methanol / 0.17 h / 0 °C

3: 57 percent / CuSO₄, CSA / 24 h / Ambient temperature

4: 92 percent / CH₂Cl₂; pyridine / -20 - 20 °C

5: 82 percent / n-Bu₄NI / dimethylformamide / 1.5 h / 60 °C

6: 92 percent / tetrahydrothiophene 1,1-dioxide / 5 h / 110 °C

7: 76 percent / HMDSLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 - -10 °C

With 2,4,6-trimethyl-pyridine; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; copper(II) sulfate; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; sulfolane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)00018-9

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranose (131234-07-6) → 2-{(3aS,4R,6S,7R,7aR)-4-[(Z)-2-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-vinyl]-6-tert-butoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-isoindole-1,3-dione (155793-68-3)

Guidance literature:

Multi-step reaction with 8 steps

1: HBr / CH₂Cl₂; acetic acid / 4 h

2: 7.4 g / AgOTf, sym-collidine / CH₂Cl₂ / 2 h / 0 °C

3: 5.5 g / MeONa / methanol / 0.17 h / 0 °C

4: 57 percent / CuSO₄, CSA / 24 h / Ambient temperature

5: 92 percent / CH₂Cl₂; pyridine / -20 - 20 °C

6: 82 percent / n-Bu₄NI / dimethylformamide / 1.5 h / 60 °C

7: 92 percent / tetrahydrothiophene 1,1-dioxide / 5 h / 110 °C

8: 76 percent / HMDSLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 - -10 °C

With 2,4,6-trimethyl-pyridine; camphor-10-sulfonic acid; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; copper(II) sulfate; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; sulfolane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)00018-9

upstream raw materials:

benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranosyl bromide

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranose

2-((2S,3R,4R,5R,6R)-2-tert-Butoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione