C₆₉H₈₂N₄O₁₉

Base Information

• Chemical Name: C₆₉H₈₂N₄O₁₉
• CAS No.: 187173-19-9
• Molecular Formula: C₆₉H₈₂N₄O₁₉
• Molecular Weight: 1271.43
• Mol file: 187173-19-9.mol

Synonyms:C₆₉H₈₂N₄O₁₉

Chemical Property of C₆₉H₈₂N₄O₁₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₆₉H₈₂N₄O₁₉

There total 10 articles about C₆₉H₈₂N₄O₁₉ 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: 73.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) + (2S,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol (187173-18-8) → C69H82N4O19 (187173-19-9)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -40 - 20 ℃; for 4h;

DOI:10.1016/S0968-0896(96)00180-0

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol (125631-33-6,125647-51-0,132871-89-7,132871-95-5,132871-96-6,123487-65-0) → C69H82N4O19 (187173-19-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 46 percent / PPTS / dimethylformamide / 24 h

2: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) DMF, 100 deg C, 20 min

3: 81 percent / pyridine / Ambient temperature

4: 85 percent / NaBH₃CN, mol. sieves 3A, TFA / dimethylformamide / 48 h / 0 - 20 °C

5: 90 percent / NaH / dimethylformamide / 3 h / -15 °C

6: 87 percent / DDQ / CH₂Cl₂; H₂O / 5 h / Ambient temperature

7: 100 percent / pyridine / 7 h / Ambient temperature

8: 90 percent / NaN₃ / dimethylformamide / 32 h / 20 - 40 °C

9: 48 percent / NIS, AgOTf / CH₂Cl₂ / 20 h / Ambient temperature

10: 96 percent / MeONa / methanol / 36 h / Ambient temperature

11: 73 percent / AgOTf, mol. sieves 4A, collidine / CH₂Cl₂ / 4 h / -40 - 20 °C

With pyridine; 2,3,5-trimethyl-pyridine; N-iodo-succinimide; sodium azide; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(96)00180-0

Reference yield:

octyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (118249-72-2) → C69H82N4O19 (187173-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / NIS, AgOTf / CH₂Cl₂ / 20 h / Ambient temperature

2: 96 percent / MeONa / methanol / 36 h / Ambient temperature

3: 73 percent / AgOTf, mol. sieves 4A, collidine / CH₂Cl₂ / 4 h / -40 - 20 °C

With 2,3,5-trimethyl-pyridine; N-iodo-succinimide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/S0968-0896(96)00180-0

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

(2S,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol

octyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-6-Azidomethyl-4-benzyloxy-5-methoxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide