5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-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)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 256348-59-1
• Molecular Formula: C₅₆H₆₆N₄O₂₀
• Molecular Weight: 1115.15

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

There total 15 articles about 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-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: 88.0%

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-97-5) + 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)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (256348-59-1)

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)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (256348-59-1)

Guidance literature:

Multi-step reaction with 14 steps

1: HCl

2: CSA / tetrahydrofuran

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

4: aq. AcOH

5: pyridine / CH₂Cl₂

6: 75 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 / 2-methyl-propan-2-ol

14: 88 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; acetic acid; potassium bromide; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1: Glycosidation / 2: Acetalization / 3: Alkylation / 4: Hydrolysis / 5: Acetylation / 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

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (256348-59-1)

Guidance literature:

Multi-step reaction with 15 steps

1: aq. Na₂CO₃

2: HCl

3: CSA / tetrahydrofuran

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

5: aq. AcOH

6: pyridine / CH₂Cl₂

7: 75 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

8: NaOMe; MeOH

9: CSA / acetone

10: DMAP; pyridine / CH₂Cl₂

11: aq. AcOH

12: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

13: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

15: 88 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 carbonate; acetic acid; potassium bromide; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1: Acylation / 2: Glycosidation / 3: Acetalization / 4: Alkylation / 5: Hydrolysis / 6: Acetylation / 7: Glycosidation / 8: Deacetylation / 9: Acetalization / 10: Acetylation / 11: Hydrolysis / 12: Oxidation / 13: Oxidation / 14: Esterification / 15: Glycosidation;

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

upstream raw materials:

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

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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