(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

Base Information

• Chemical Name: (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
• CAS No.: 858127-25-0
• Molecular Formula: C₄₇H₄₉N₃O₁₁
• Molecular Weight: 831.92
• Mol file: 858127-25-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

(2R,3R,4R,5R,6S)-5-Azido-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol + benzaldehyde dimethyl acetal (1125-88-8) → (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 (858127-25-0)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; at 70 ℃; for 3h;

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 → (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 (858127-25-0)

Guidance literature:

Multi-step reaction with 3 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

With ammonium hydroxide; 4 A molecular sieve; camphor-10-sulfonic acid; ytterbium(III) triflate; In methanol; acetonitrile;

DOI:10.1021/jo050301x

Reference yield:

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 (858127-24-9) → (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 (858127-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NH₄OH / methanol / 3 h / 20 °C

2: 152 mg / camphorsulfonic acid / acetonitrile / 3 h / 70 °C

With ammonium hydroxide; camphor-10-sulfonic acid; In methanol; acetonitrile;

DOI:10.1021/jo050301x

upstream raw materials:

benzaldehyde dimethyl acetal

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

p-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

Downstream 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-{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