5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 256348-58-0
• Molecular Formula: C₆₁H₇₀N₄O₁₉
• Molecular Weight: 1163.24

Synonyms:5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 14 articles about 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic 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: 89.0%

(2R,3S,4S,5R,6R)-5-Acetoxy-4-benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (110255-42-0) + 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose (241129-78-2) → 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256348-58-0)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In toluene; at -20 ℃;

DOI:10.1016/S0960-894X(99)00550-8

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256348-58-0)

Guidance literature:

Multi-step reaction with 13 steps

1: HCl

2: CSA / tetrahydrofuran

3: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

4: 61 percent / NaBH₃CN; HCl / tetrahydrofuran

5: 83 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

6: NaOMe; MeOH

7: CSA / acetone

8: DMAP; pyridine / CH₂Cl₂

9: aq. AcOH

10: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

11: NaClO₂; aq. NaH₂PO₄

13: 89 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C

With pyridine; hydrogenchloride; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; barium dihydroxide; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; t-butyldimethylsiyl triflate; sodium methylate; sodium cyanoborohydride; acetic acid; potassium bromide; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Glycosidation / 2: Acetalization / 3: Alkylation / 4: Ring cleavage / 5: Glycosidation / 6: Deacetylation / 7: Acetalization / 8: Acetylation / 9: Hydrolysis / 10: Oxidation / 11: Oxidation / 12: Esterification / 13: Glycosidation;

DOI:10.1016/S0960-894X(99)00550-8

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (256348-58-0)

Guidance literature:

Multi-step reaction with 14 steps

1: aq. Na₂CO₃

2: HCl

3: CSA / tetrahydrofuran

4: 78 percent / BaO; Ba(OH)2*8H₂O / dimethylformamide

5: 61 percent / NaBH₃CN; HCl / tetrahydrofuran

6: 83 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

7: NaOMe; MeOH

8: CSA / acetone

9: DMAP; pyridine / CH₂Cl₂

10: aq. AcOH

11: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

12: NaClO₂; aq. NaH₂PO₄

14: 89 percent / t-butyldimethylsilyl triflate; 4 Angstroem sieves / toluene / -20 °C

With pyridine; hydrogenchloride; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; barium dihydroxide; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; t-butyldimethylsiyl triflate; sodium methylate; sodium cyanoborohydride; sodium carbonate; acetic acid; potassium bromide; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Acylation / 2: Glycosidation / 3: Acetalization / 4: Alkylation / 5: Ring cleavage / 6: Glycosidation / 7: Deacetylation / 8: Acetalization / 9: Acetylation / 10: Hydrolysis / 11: Oxidation / 12: Oxidation / 13: Esterification / 14: Glycosidation;

DOI:10.1016/S0960-894X(99)00550-8

upstream raw materials:

(2R,3S,4S,5R,6R)-5-Acetoxy-4-benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-1-O-trichloroacetimidoyl-D-glucopyranose

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

(+)-D-glucosamine hydrochloride

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