[(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

Base Information

• Chemical Name: [(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
• CAS No.: 538370-39-7
• Molecular Formula: C₅₁H₆₅N₃O₁₀Si
• Molecular Weight: 908.177

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 5 articles about [(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 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,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 (538370-39-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2: CH₂Cl₂ / -78 °C

3: CAN / acetonitrile; H₂O

4: imidazole

With 1H-imidazole; 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:

phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside S-oxide → [(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 (538370-39-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2: CH₂Cl₂ / -78 °C

3: CAN / acetonitrile; H₂O

4: imidazole

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium(IV) nitrate; In dichloromethane; water; acetonitrile;

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

Reference yield:

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 (538370-37-5) → [(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 (538370-39-7)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / -78 °C

2: CAN / acetonitrile; H₂O

3: imidazole

With 1H-imidazole; ammonium cerium(IV) nitrate; In dichloromethane; water; acetonitrile;

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

upstream raw materials:

tert-butyldimethylsilyl chloride

(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

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:

C₇₁H₈₆N₆O₁₄Si

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