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

Base Information

• Chemical Name: Acetic acid (3R,4S,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 756496-85-2
• Molecular Formula: C₂₄H₃₄O₁₂
• Molecular Weight: 514.527

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 3 articles about Acetic acid (3R,4S,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-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: 70.0%

benzyl alcohol (100-51-6,185532-71-2) + (3-O-allyl-β-D-galactopyranosyl)-(1->4)-[1,2-O-(1-(β-methoxyethylidene)]-α-D-glucopyranose (756496-84-1) → Acetic acid (3R,4S,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (756496-85-2)

Guidance literature:

With trifluorormethanesulfonic acid; 3 A molecular sieve; In acetonitrile; at 0 ℃;

DOI:10.1002/ejoc.200300807

Reference yield:

(2S,3R,4S,5R,6R)-2-((3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol → Acetic acid (3R,4S,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (756496-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / methanol / 15 h / 60 °C

1.2: 11.84 g / Bu₄NI / toluene / 17 h / 60 °C

2.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

With trifluorormethanesulfonic acid; 3 A molecular sieve; di(n-butyl)tin oxide; In methanol; acetonitrile;

DOI:10.1002/ejoc.200300807

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (299174-87-1) → Acetic acid (3R,4S,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (756496-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOMe; MeOH / 4 h

2.1: Bu₂SnO / methanol / 15 h / 60 °C

2.2: 11.84 g / Bu₄NI / toluene / 17 h / 60 °C

3.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

With methanol; trifluorormethanesulfonic acid; 3 A molecular sieve; sodium methylate; di(n-butyl)tin oxide; In methanol; acetonitrile; 1.1: Zemplen deacetylation;

DOI:10.1002/ejoc.200300807

upstream raw materials:

benzyl alcohol

(3-O-allyl-β-D-galactopyranosyl)-(1->4)-[1,2-O-(1-(β-methoxyethylidene)]-α-D-glucopyranose

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

Downstream raw materials:

benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(p-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-2-O-benzoyl-3-O-benzyl-6-O-(thexyldimethylsilyl)-β-D-glucopyranoside

Benzoic acid (2R,3R,4S,5R,6R)-2,4-bis-benzyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-5-[(2S,4aR,6S,7R,8S,8aR)-8-hydroxy-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-3-yl ester

benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-3-O-benzyl-2,6-di-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside

benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

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