1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Base Information

• Chemical Name: 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol
• CAS No.: 260392-75-4
• Molecular Formula: C₆₃H₇₅N₃O₁₀Si
• Molecular Weight: 1062.39
• Mol file: 260392-75-4.mol

Synonyms:1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Chemical Property of 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

There total 25 articles about 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 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: 65.0%

1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol (132437-54-8) + 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl bromide (220679-83-4) → 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol (260392-75-4)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; In dichloromethane; at 20 ℃; for 24h;

Reference yield: 65.0%

1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol (132437-54-8) + 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl bromide (220679-83-4) → [(2R,3S,4R,5R,6S)-6-((1S,2R,3S,4S,5R,6S)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexyloxy)-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane + 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol (260392-75-4)

Guidance literature:

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 72h; Yields of byproduct given;

DOI:10.1002/(SICI)1521-3773(19981231)37:24<3423::AID-ANIE3423>3.0.CO;2-I

Reference yield:

benzyl bromide (100-39-0) → 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol (260392-75-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / TBAI; NaH / toluene / 6 h

2: 71 percent / Et₃SiH; TFA / CH₂Cl₂ / 10 h

3: 94 percent / NH₂NH₂*H₂O / ethanol / 48 h / Heating

4: 98 percent / TfN₃; DMAP / CH₂Cl₂; acetonitrile / 6 h / 20 °C

5: 93 percent / KN(SiMe₃) / toluene; tetrahydrofuran / 0.5 h / 20 °C

6: Br₂ / CH₂Cl₂ / 1 h / 20 °C

7: 65 percent / TBABr; molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / 20 °C

With triethylsilane; dmap; 4 A molecular sieve; triflic azide; tetrabutylammomium bromide; bromine; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; hydrazine hydrate; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; 1: Etherification / 2: Reduction / 3: Hydrazinolysis / 4: Substitution / 5: Etherification / 6: Bromination / 7: Etherification;

upstream raw materials:

1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl bromide

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

benzyl bromide

Downstream raw materials:

(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol