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

Base Information

• Chemical Name: 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
• CAS No.: 187173-17-7
• Molecular Formula: C₅₆H₆₇N₃O₁₁
• Molecular Weight: 958.161
• Mol file: 187173-17-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 48.0%

octyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (118249-72-2) + 4-pentenyl 6-azido-2-O-benzoyl-3-O-benzyl-6-deoxy-4-O-methyl-α-D-mannopyranoside (187173-16-6) → 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 (187173-17-7)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; for 20h; Ambient temperature;

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) → 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 (187173-17-7)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; N-iodo-succinimide; sodium azide; 3 A molecular sieve; 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 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 → 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 (187173-17-7)

Guidance literature:

Multi-step reaction with 8 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

8: 48 percent / NIS, AgOTf / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; N-iodo-succinimide; sodium azide; 3 A molecular sieve; silver trifluoromethanesulfonate; 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:

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

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

(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

Downstream raw materials:

(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

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