(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
• CAS No.: 908845-58-9
• Molecular Formula: C₆₀H₆₉N₃O₁₆
• Molecular Weight: 1088.22
• Mol file: 908845-58-9.mol

Synonyms:(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Chemical Property of (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

There total 1 articles about (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-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: 84.0%

(2R,4aR,6S,7R,8S,8aR)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-7,8-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (908845-57-8) → (2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol (908845-58-9)

Guidance literature:

With 4 A molecular sieve; sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/j.tetlet.2006.06.001

Reference yield: 92.0%

(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol (908845-58-9) + methyl iodide (74-88-4) → C61H71N3O16 (908845-59-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/j.tetlet.2006.06.001

Reference yield:

(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-Azido-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol (908845-58-9) → C75H91N5O18Si

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / NaH / dimethylformamide / 50 °C

2: H₂ / Pd/C / ethanol; ethyl acetate

3: 55 percent / NaO(t-Bu) / Pd₂(dba)3; (S)-BINAP / toluene / 6 h / 80 °C

4: toluene / 120 h / 100 °C

With hydrogen; sodium hydride; sodium t-butanolate; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2006.06.001

upstream raw materials:

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

Downstream raw materials:

C₆₁H₇₁N₃O₁₆

dapiramicin B

(2R,3R,4S,5R,6R)-3,4-Bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-5-[(2S,3R,4S,5R,6R)-5-methoxy-3,4-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-ylamine

C₇₅H₉₁N₅O₁₈Si