(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

Base Information

• Chemical Name: (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
• CAS No.: 908845-57-8
• Molecular Formula: C₆₀H₆₇N₃O₁₆
• Molecular Weight: 1086.2
• Mol file: 908845-57-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 54.0%

(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Azido-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (908845-56-7) + p-methoxybenzyl chloride (824-94-2) → (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)

Guidance literature:

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; 15-crown-5; In dimethyl sulfoxide; at 70 ℃;

DOI:10.1016/j.tetlet.2006.06.001

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:

(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) → C75H91N5O18Si

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / NaBH₃CN; trifluoroacetic acid; 4 Angstroem molecular sieves / dimethylformamide / 50 °C

2: 92 percent / NaH / dimethylformamide / 50 °C

3: H₂ / Pd/C / ethanol; ethyl acetate

4: 55 percent / NaO(t-Bu) / Pd₂(dba)3; (S)-BINAP / toluene / 6 h / 80 °C

5: toluene / 120 h / 100 °C

With 4 A molecular sieve; hydrogen; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; 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,8R,8aS)-6-((2R,3S,4R,5R,6R)-6-Azido-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

p-methoxybenzyl chloride

Downstream raw materials:

(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

dapiramicin B

C₆₁H₇₁N₃O₁₆

(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