Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 87171-80-0
• Molecular Formula: C₂₉H₃₆O₁₅S
• Molecular Weight: 656.662

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-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:

benzyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D--galacto-pyranosyl)-β-D-glucopyranoside (68115-82-2) → Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester (87171-80-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NBS, BaCO₃ / CCl₄; various solvent(s) / 3.5 h / Heating

2: 1.)H₂, MeOH, Pd-C, BaCO₃ 2.)Ac₂O-pyridine, 3.)H₂, EtOAc, Et₃N, Raney-Ni 4.) H₂O

3: HBr / CH₂Cl₂; acetic acid / 1 h / 0 - 5 °C

4: 1.) Thiourea, acetone reflux 10 h.,2.)K₂S₂O₅, H₂O-CHCl₃ reflux 2 h.

With N-Bromosuccinimide; hydrogen bromide; barium carbonate; In tetrachloromethane; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(83)88034-3

Reference yield:

1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-ga-lactopyranosyl)-D-glucopyranose (87171-77-5) → Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester (87171-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr / CH₂Cl₂; acetic acid / 1 h / 0 - 5 °C

2: 1.) Thiourea, acetone reflux 10 h.,2.)K₂S₂O₅, H₂O-CHCl₃ reflux 2 h.

With hydrogen bromide; In dichloromethane; acetic acid;

DOI:10.1016/0008-6215(83)88034-3

Reference yield:

benzyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside (87171-67-3) → Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester (87171-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.)H₂, MeOH, Pd-C, BaCO₃ 2.)Ac₂O-pyridine, 3.)H₂, EtOAc, Et₃N, Raney-Ni 4.) H₂O

2: HBr / CH₂Cl₂; acetic acid / 1 h / 0 - 5 °C

3: 1.) Thiourea, acetone reflux 10 h.,2.)K₂S₂O₅, H₂O-CHCl₃ reflux 2 h.

With hydrogen bromide; In dichloromethane; acetic acid;

DOI:10.1016/0008-6215(83)88034-3

upstream raw materials:

Benzoic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

benzyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D--galacto-pyranosyl)-β-D-glucopyranoside

1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-ga-lactopyranosyl)-D-glucopyranose

benzyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside

Downstream raw materials:

6-(5-cholesten-3β-yloxy)hexyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl--4-O-benzoyl-6-deoxy-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

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