2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

Base Information

• Chemical Name: 2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione
• CAS No.: 177421-31-7
• Molecular Formula: C₃₀H₂₉NO₆S
• Molecular Weight: 531.629
• Mol file: 177421-31-7.mol

Synonyms:

Chemical Property of 2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

There total 3 articles about 2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-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: 66.0%

benzyl bromide (100-39-0) + 2-((4aR,6S,7R,8R,8aS)-8-Hydroxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (177421-30-6) → 2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (177421-31-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) r.t., 0.5 h, 2.) r.t., overnight;

DOI:10.1080/07328309608005653

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-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (177421-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / acetonitrile / 16 h

2: 66 percent / NaH / dimethylformamide / 1.) r.t., 0.5 h, 2.) r.t., overnight

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005653

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → 2-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (177421-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / 1 h / Ambient temperature

2: p-TsOH*H₂O / acetonitrile / 16 h

3: 66 percent / NaH / dimethylformamide / 1.) r.t., 0.5 h, 2.) r.t., overnight

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005653

upstream raw materials:

benzyl bromide

2-((4aR,6S,7R,8R,8aS)-8-Hydroxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

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

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

Downstream raw materials:

3-Azidopropyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

3-Azidopropyl O-(3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

3-Azidopropyl O-(3-O-benzyl-2-deoxy-4,6-di-O-isopropylidene-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside