Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester
CAS No.:126365-89-7
Molecular Formula:C₃₇H₄₈O₈
Molecular Weight:620.783
Hs Code.:

Synonyms:Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

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Chemical Property of Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

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Technology Process of Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

There total 1 articles about Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl 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: 32.0%

: 98-88-4
benzoyl chloride

: 120269-74-1
(2R,3R,6S)-6-((2R,5R,6S)-5-Benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxy)-heptane-1,3,6-triol

: 126365-89-7
Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

: 126365-90-0
C₄₄H₅₂O₉

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1248/cpb.37.1717

Reference yield: 100.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 126365-89-7
Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

: 126419-23-6
(2R,3R,6S)-1-benzoyloxy-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-heptane

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1248/cpb.37.1717

Reference yield:

: 126365-89-7
Benzoic acid (2R,3R,6S)-6-((2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyl-tetrahydro-pyran-2-yl)-3,6-dihydroxy-2-(4-methoxy-benzyloxy)-heptyl ester

: (2S,3R,6R)-6-[(1S,4R,5R)-1,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-5-(4-methoxy-benzyloxy)-1-methyl-hexyl]-3-ethyl-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 95 percent / aq. KOH / methanol / 0.5 h / 55 °C

3: 1) DMSO, (COCl₂)2, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) CH₂Cl₂, -78 to -15 deg C

4: 96 percent / Ph₃P / benzene / 0.5 h / 80 °C

5: 84 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -20 °C

6: 1) NaH / 1) DMF, 2) DMF, 50 deg C, 2 h

7: MeOH, CSA / 0.25 h / Ambient temperature

With methanol; potassium hydroxide; n-butyllithium; (COCl₂)2; camphor-10-sulfonic acid; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.37.1717