(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

Base Information

Chemical Name:(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne
CAS No.:120269-85-4
Molecular Formula:C₄₄H₇₂O₇Si₂
Molecular Weight:769.222
Hs Code.:

(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

Synonyms:(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

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Chemical Property of (3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

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Technology Process of (3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

There total 13 articles about (3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne 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: 83.0%

: (2S,3R,6R)-6-[(1S,4R,5R)-7,7-Dibromo-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-1-methyl-hept-6-enyl]-3-ethyl-3-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran

: 120269-85-4
(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.666667h;
DOI:10.1248/cpb.37.1717

Reference yield:

: 120269-75-2
(2R,3R,6S)-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptan-1-ol

: 120269-85-4
(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

Guidance literature:: Multi-step reaction with 8 steps

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

2: 96 percent / Ph₃P / benzene / 0.5 h / 80 °C

3: 84 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -20 °C

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

5: MeOH, CSA / 0.25 h / Ambient temperature

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

7: 88 percent / Ph₃P / CH₂Cl₂ / 0.33 h / -78 °C

8: 83 percent / LDA / tetrahydrofuran / 0.67 h / -70 °C

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

Reference yield:

: 120269-83-2
(2R,3R,6S)-3,6-bis(tert-butyldimethylsilyloxy)-6-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-2-(4-methoxybenzyloxy)heptan-1-ol

: 120269-85-4
(3R,4R,7S)-4,7-bis(tert-butyldimethylsilyloxy)-7-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-3-(4-methoxybenzyloxy)oct-1-yne

Guidance literature:: Multi-step reaction with 3 steps

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

2: 88 percent / Ph₃P / CH₂Cl₂ / 0.33 h / -78 °C

3: 83 percent / LDA / tetrahydrofuran / 0.67 h / -70 °C

With (COCl₂)2; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.37.1717