4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside

Base Information

• Chemical Name: 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside
• CAS No.: 187173-16-6
• Molecular Formula: C₂₆H₃₁N₃O₆
• Molecular Weight: 481.549
• Mol file: 187173-16-6.mol

Synonyms:4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside

Chemical Property of 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside

There total 8 articles about 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside 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: 90.0%

Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (187173-15-5) → 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside (187173-16-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 - 40 ℃; for 32h;

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) → 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside (187173-16-6)

Guidance literature:

Multi-step reaction with 8 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

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

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

Reference yield:

4-pentenyl 4,6-O-(4-methoxybenzylidene)-α-D-mannopyranoside → 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside (187173-16-6)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 81 percent / pyridine / Ambient temperature

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

4: 90 percent / NaH / dimethylformamide / 3 h / -15 °C

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

6: 100 percent / pyridine / 7 h / Ambient temperature

7: 90 percent / NaN₃ / dimethylformamide / 32 h / 20 - 40 °C

With pyridine; sodium azide; 3 A molecular sieve; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;

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

upstream raw materials:

Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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

4-pentenyl 2-O-benzoyl-3-O-benzyl-4-O-methyl-α-D-mannopyranoside

4-pentenyl 2-O-benzoyl-3-O-benzyl-6-O-(4-methoxybenzyl)-α-D-mannopyranoside

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

(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

C₆₉H₈₂N₄O₁₉

Benzoic acid (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-yl ester