(1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Base Information

• Chemical Name: (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol
• CAS No.: 637329-58-9
• Molecular Formula: C₆₁H₆₃N₃O₁₀
• Molecular Weight: 998.185
• Mol file: 637329-58-9.mol

Synonyms:(1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Chemical Property of (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

There total 10 articles about (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol 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: 62.0%

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol (637329-55-6) → (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol (637329-58-9)

Guidance literature:

With sodium acetate; palladium dichloride; In acetic acid; at 20 ℃; for 6h;

DOI:10.1055/s-2003-40339

Reference yield:

D-myo-inositol (87-89-8) → (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol (637329-58-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 56 percent / H₂SO₄ / dimethylsulfoxide / 55 °C

2: 100 percent / NaH / dimethylformamide / -20 °C

3: 80 percent / CH₃COOH

4: 100 percent / pyridine / CH₂Cl₂ / -78 °C

5: 100 percent / DMAP; pyridine / 20 °C

6: 68 percent / H₂O / dimethylformamide / 90 °C

7: 71 percent / dppb / Pd₂(dba)3 / tetrahydrofuran / 70 °C

8: NaOMe / methanol; tetrahydrofuran

9: 42 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / -25 - 20 °C

10: 62 percent / aq. AcONa; PdCl₂ / acetic acid / 6 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; water; sodium methylate; sodium acetate; sodium hydride; acetic acid; 1,4-di(diphenylphosphino)-butane; palladium dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1055/s-2003-40339

Reference yield:

1,4,5,6-tetra-O-benzyl-myo-inositol (28140-40-1) → (1S,2R,3S,4R,5S,6R)-2-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol (637329-58-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / pyridine / CH₂Cl₂ / -78 °C

2: 100 percent / DMAP; pyridine / 20 °C

3: 68 percent / H₂O / dimethylformamide / 90 °C

4: 71 percent / dppb / Pd₂(dba)3 / tetrahydrofuran / 70 °C

5: NaOMe / methanol; tetrahydrofuran

6: 42 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / -25 - 20 °C

7: 62 percent / aq. AcONa; PdCl₂ / acetic acid / 6 h / 20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; sodium methylate; sodium acetate; 1,4-di(diphenylphosphino)-butane; palladium dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1055/s-2003-40339

upstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol

D-myo-inositol

1,4,5,6-tetra-O-benzyl-myo-inositol

2,3-O-(D-1,7,7-trimethylbicyclo[2.2.1]hept-6-ylidene)-D-myo-inositol