Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 88988-47-0
• Molecular Formula: C₅₉H₆₄O₁₂
• Molecular Weight: 965.15

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-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: 95.0%

allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (83921-79-3) + 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranosyl chloride (89016-59-1) → Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (88988-47-0)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(83)88400-6

Reference yield:

2-O-acetyl-3,4,6-tetra-O-benzyl-α-D-glucopyranose (88988-46-9) → Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (88988-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂, DMF / CH₂Cl₂

2: 95 percent / AgOSO₂CF₃, molecular sieves 4A / 1,2-dichloro-ethane

With thionyl chloride; 4 A molecular sieve; silver trifluoromethanesulfonate; N,N-dimethyl-formamide; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(83)88400-6

Reference yield:

allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (88999-17-1) → Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (88988-47-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / PdCl₂, AcONa-aq. AcOH

2: SOCl₂, DMF / CH₂Cl₂

3: 95 percent / AgOSO₂CF₃, molecular sieves 4A / 1,2-dichloro-ethane

With thionyl chloride; 4 A molecular sieve; sodium acetate; silver trifluoromethanesulfonate; acetic acid; N,N-dimethyl-formamide; palladium dichloride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(83)88400-6

upstream raw materials:

allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranosyl chloride

2-O-acetyl-3,4,6-tetra-O-benzyl-α-D-glucopyranose

allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

(2S,3R,4R,5R,6R)-2-((2R,3R,4S,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

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