(R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester

Base Information

• Chemical Name: (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester
• CAS No.: 197720-15-3
• Molecular Formula: C₇₄H₉₂N₄O₁₅
• Molecular Weight: 1277.56

Synonyms:

Chemical Property of (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester

There total 13 articles about (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl 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:

(2R,3R,45,5R,6R)-methyl 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate (57039-37-9) → (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester (197720-15-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) PhCHO, HCO₂H; 2.) NaH; 3.) NaBH₃CN

2: pyr / CH₂Cl₂

3: NaN₃ / dimethylformamide

4: H₂S / pyridine; H₂O

5: Et₃N / methanol

6: LiOH / tetrahydrofuran; methanol; H₂O

7: 82 percent / BOP, diisopropylethylamine / dimethylformamide

8: HCl / ethyl acetate

9: BOP, diisopropylethylamine / dimethylformamide

10: HCl / ethyl acetate

11: BOP, diisopropylethylamine / dimethylformamide

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; sodium azide; hydrogen sulfide; sodium hydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzaldehyde; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01764-4

Reference yield:

benzyl bromide (100-39-0) → (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester (197720-15-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) PhCHO, HCO₂H; 2.) NaH; 3.) NaBH₃CN

2: pyr / CH₂Cl₂

3: NaN₃ / dimethylformamide

4: H₂S / pyridine; H₂O

5: Et₃N / methanol

6: LiOH / tetrahydrofuran; methanol; H₂O

7: 82 percent / BOP, diisopropylethylamine / dimethylformamide

8: HCl / ethyl acetate

9: BOP, diisopropylethylamine / dimethylformamide

10: HCl / ethyl acetate

11: BOP, diisopropylethylamine / dimethylformamide

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; sodium azide; hydrogen sulfide; sodium hydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzaldehyde; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01764-4

Reference yield:

methyl 2,6-anhydro-3,4,7-tri-O-benzyl-D-glycero-L-manno-hepturonate (197720-07-3) → (R)-2-[((2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carbonyl)-amino]-N-((2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-octylcarbamoyl-tetrahydro-pyran-3-yl)-succinamic acid methyl ester (197720-15-3)

Guidance literature:

Multi-step reaction with 10 steps

1: pyr / CH₂Cl₂

2: NaN₃ / dimethylformamide

3: H₂S / pyridine; H₂O

4: Et₃N / methanol

5: LiOH / tetrahydrofuran; methanol; H₂O

6: 82 percent / BOP, diisopropylethylamine / dimethylformamide

7: HCl / ethyl acetate

8: BOP, diisopropylethylamine / dimethylformamide

9: HCl / ethyl acetate

10: BOP, diisopropylethylamine / dimethylformamide

With pyridine; hydrogenchloride; lithium hydroxide; sodium azide; hydrogen sulfide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01764-4

upstream raw materials:

(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carboxylic acid

(2R,3R,45,5R,6R)-methyl 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate

n-Octylamine

benzyl bromide

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