Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 256348-55-7
• Molecular Formula: C₃₉H₄₇NO₁₄
• Molecular Weight: 753.8
• Mol file: 256348-55-7.mol

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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

Chemical Property:

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl 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:

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 (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (256348-55-7)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; hydrogenchloride; methanol; dmap; barium dihydroxide; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Glycosidation / 2: Acetalization / 3: Alkylation / 4: Hydrolysis / 5: Acetylation / 6: Glycosidation / 7: Deacetylation / 8: Acetalization / 9: Acetylation / 10: Hydrolysis;

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

Reference yield:

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5) → Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (256348-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂

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

3: NaOMe; MeOH

4: CSA / acetone

5: DMAP; pyridine / CH₂Cl₂

6: aq. AcOH

With pyridine; methanol; dmap; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; In dichloromethane; acetone; 1: Acetylation / 2: Glycosidation / 3: Deacetylation / 4: Acetalization / 5: Acetylation / 6: Hydrolysis;

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

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (256348-55-7)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; hydrogenchloride; methanol; dmap; barium dihydroxide; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; sodium carbonate; acetic acid; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Acylation / 2: Glycosidation / 3: Acetalization / 4: Alkylation / 5: Hydrolysis / 6: Acetylation / 7: Glycosidation / 8: Deacetylation / 9: Acetalization / 10: Acetylation / 11: Hydrolysis;

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

upstream raw materials:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl chloroformate

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Downstream 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

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

methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside