(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

Base Information

• Chemical Name: (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
• CAS No.: 120269-83-2
• Molecular Formula: C₄₃H₇₄O₈Si₂
• Molecular Weight: 775.227

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (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

There total 10 articles about (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 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:

(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 (120269-75-2) → (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 (120269-83-2)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(00)80703-0

Reference yield:

(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 (120269-74-1) → (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 (120269-83-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 64 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 95 percent / aq. KOH / methanol / 0.5 h / 55 °C

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

5: 96 percent / Ph₃P / benzene / 0.5 h / 80 °C

6: 84 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -20 °C

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

8: MeOH, CSA / 0.25 h / Ambient temperature

With pyridine; 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

Reference yield:

(2S,3R,6R)-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptanal (126365-91-1) → (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 (120269-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / Ph₃P / benzene / 0.5 h / 80 °C

2: 84 percent / n-BuLi / hexane; tetrahydrofuran / -78 - -20 °C

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

4: MeOH, CSA / 0.25 h / Ambient temperature

With methanol; n-butyllithium; camphor-10-sulfonic acid; sodium hydride; triphenylphosphine; In tetrahydrofuran; hexane; benzene;

DOI:10.1248/cpb.37.1717

upstream raw materials:

(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

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

(2S,3R,6R)-6-<(2R,5R,6S)-5-benzyloxy-5-ethyl-6-methyltetrahydropyran-2-yl>-3,6-bis(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptanal

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

Downstream raw materials:

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

(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

(2S,5R,6R)-8-<(2RS,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-yne-2,5-diol

(2S,5R,6R,7Z)-8-<(2R,3R,5S,6S)-6-<(1S,2R)-1-ethyl-2-hydroxybutyl>-2-methoxy-3,5-dimethyltetrahydropyran-2-yl>-2-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-6-(4-methoxybenzyloxy)oct-7-ene-2,5-diol

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