2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol
• CAS No.: 858127-27-2
• Molecular Formula: C₇₄H₇₇N₃O₁₆
• Molecular Weight: 1264.44
• Mol file: 858127-27-2.mol

Synonyms:2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Chemical Property of 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

There total 8 articles about 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-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: 89.0%

p-methoxyphenyl 3,4,6-tri-O-benzyl-2-O-methoxycarbonyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-azido-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside (858127-26-1) → 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (858127-27-2)

Guidance literature:

With potassium carbonate; In methanol; at 40 ℃; for 8h;

DOI:10.1021/jo050301x

Reference yield:

Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2,2,2-trifluoro-N-phenyl-acetimidoyloxy)-tetrahydro-pyran-4-yl ester → 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (858127-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / 4 Angstroem AW 300 molecular sieves; Yb(OTf)3 / acetonitrile / 0 - 20 °C

2: aq. NH₄OH / methanol / 3 h / 20 °C

3: 152 mg / camphorsulfonic acid / acetonitrile / 3 h / 70 °C

4: 75 percent / 5 Angstroem AW molecular sieves / 1,2-dichloro-ethane; cyclohexane / 20 °C

5: 89 percent / K₂CO₃ / methanol / 8 h / 40 °C

With ammonium hydroxide; 4 A molecular sieve; 5A molecular sieve; camphor-10-sulfonic acid; potassium carbonate; ytterbium(III) triflate; In methanol; cyclohexane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jo050301x

Reference yield:

Carbonic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl ester methyl ester → 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (858127-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 658 mg / DIPEA / CH₂Cl₂ / 36 h / 20 °C

2: 75 percent / 5 Angstroem AW molecular sieves / 1,2-dichloro-ethane; cyclohexane / 20 °C

3: 89 percent / K₂CO₃ / methanol / 8 h / 40 °C

With 5A molecular sieve; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; cyclohexane; 1,2-dichloro-ethane;

DOI:10.1021/jo050301x

upstream raw materials:

p-methoxyphenyl 3,4,6-tri-O-benzyl-2-O-methoxycarbonyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-azido-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester

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

p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside