(2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

• Chemical Name: (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
• CAS No.: 915221-66-8
• Molecular Formula: C₄₅H₅₁N₃O₁₀
• Molecular Weight: 793.914

Synonyms:

Chemical Property of (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 4 articles about (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 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:

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (177943-74-7) → (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (915221-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / benzenesulfinylpiperidine; 2,4,6-tri-tert-butylpyrimidine

2: CH₂Cl₂ / -78 °C

3: CAN / acetonitrile; H₂O

With ammonium cerium(IV) nitrate; 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(03)00102-3

Reference yield:

(2R,4aR,6S,7S,8S,8aR)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (538370-38-6) → (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (915221-66-8)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile;

DOI:10.1016/S0040-4039(03)00102-3

Reference yield:

phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside S-oxide → (2R,4aR,6S,7S,8S,8aS)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (915221-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / 2,6-di-tert-butyl-4-methylpyridine

2: CH₂Cl₂ / -78 °C

3: CAN / acetonitrile; H₂O

With 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium(IV) nitrate; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(03)00102-3

upstream raw materials:

(2R,4aR,6S,7S,8S,8aR)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Trifluoro-methanesulfonic acid (2R,4aR,6R,7S,8S,8aR)-7-benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Downstream raw materials:

[(2R,4aR,6S,7S,8S,8aR)-6-((2R,3S,4R,5R,6R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-7-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tert-butyl-dimethyl-silane

C₇₁H₈₆N₆O₁₄Si

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