Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 110236-57-2
• Molecular Formula: C₄₈H₅₅NO₁₅
• Molecular Weight: 885.962

Synonyms:Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-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: 83.0%

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside (110236-56-1) + 2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate (256348-52-4) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (110236-57-2)

Guidance literature:

With tin(II) trifluoromethanesulfonate; In dichloromethane; at 0 ℃;

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

Reference yield: 55.0%

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside (110236-56-1) + Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yl ester (103703-02-2) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (110236-57-2)

Guidance literature:

With 4 A molecular sieve; mercury dibromide; In dichloromethane;

DOI:10.1016/S0040-4039(00)85356-3

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) → Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (110236-57-2)

Guidance literature:

Multi-step reaction with 5 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

With hydrogenchloride; barium dihydroxide; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium cyanoborohydride; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Glycosidation / 2: Acetalization / 3: Alkylation / 4: Ring cleavage / 5: Glycosidation;

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

upstream raw materials:

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside

Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-2-acetoxymethyl-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yl ester

2,4,6-tri-O-acetyl-3-O-benzyl-L-idopyranosyl trichloroacetimidate

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

Methyl-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-desoxy-α-D-glucopyranosyl)-(1->4)-O-(2-O-acetyl-3,6-di-O-benzyl-α-L-idopyranosyl)-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid

Methyl-O-<6-O-acetyl-3,4-di-O-benzyl-2-desoxy-2-(trifluoracetylamino)-α-D-glucopyranosyl>-(1->4)-O-(2-O-acetyl-3,6-di-O-benzyl-α-L-idopyranosyl)-(1->4)-3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid

Methyl-3,6-di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzyliden-α-L-idopyranosyl)-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid

Methyl-4-O-(2-O-acetyl-3,6-di-O-benzyl-α-L-idopyranosyl)-3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-desoxy-α-D-glucopyranosid

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