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

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 181115-89-9
• Molecular Formula: C₇₀H₇₈O₁₈
• Molecular Weight: 1207.38

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-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: 76.0%

benzoyl chloride (98-88-4) + allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-β-D-glucopyranoside (181115-83-3) → Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (181115-89-9)

Guidance literature:

With dmap; In pyridine;

DOI:10.1016/0040-4039(96)01021-0

Reference yield:

α-hepta-O-acetylmaltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0,42385-75-1) → Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (181115-89-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / Hg(AcO)2

2: 99 percent / 1M MeONa / methanol

3: 67 percent / p-TsOH / dimethylformamide

4: 89 percent / NaH / dimethylformamide

5: 74 percent / NaCNBH₃, CF₃COOH / dimethylformamide

6: 76 percent / DMAP / pyridine

With dmap; mercury(II) diacetate; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01021-0

Reference yield:

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) → Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-allyloxy-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (181115-89-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / HBr / acetic acid

2: 71 percent / Hg(AcO)2

3: 99 percent / 1M MeONa / methanol

4: 67 percent / p-TsOH / dimethylformamide

5: 89 percent / NaH / dimethylformamide

6: 74 percent / NaCNBH₃, CF₃COOH / dimethylformamide

7: 76 percent / DMAP / pyridine

With dmap; mercury(II) diacetate; hydrogen bromide; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In pyridine; methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)01021-0

upstream raw materials:

benzoyl chloride

allyl 2,3,6-tri-O-4-methoxybenzyl-4-O-(2,3,6-tri-O-4-methoxybenzyl-α-D-glucopyranosyl)-β-D-glucopyranoside

α-hepta-O-acetylmaltosyl bromide

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose

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