(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

Base Information

Chemical Name:(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one
CAS No.:898552-00-6
Molecular Formula:C₃₀H₄₄O₇Si
Molecular Weight:544.761
Hs Code.:

(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

Synonyms:(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

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Chemical Property of (2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

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Technology Process of (2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

There total 8 articles about (2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one 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: 64.0%

: (S)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-hydroxy-6H-pyran-3-one

: 149-73-5
trimethyl orthoformate

: 898552-00-6
(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 8h;
DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

: 2-[(S)-1-(2-Ethoxy-ethoxy)-but-3-enyl]-furan

: 898552-00-6
(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / 0.12 h / -78 °C

1.2: HMPA / tetrahydrofuran / 0.5 h / -78 °C

2.1: 82 percent / PPTS / 2-methyl-propan-2-ol; H₂O / 13 h / 20 °C

3.1: 58 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / various solvents / 7 h / 40 °C

4.1: 64 percent / PPTS / CH₂Cl₂ / 8 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; various solvents; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

: Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,8aS)-7-hydroxy-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl ester

: 898552-00-6
(2S,6R)-2-Allyl-6-[(2R,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-6-methoxy-6H-pyran-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 1 h / -78 - -10 °C

2.1: n-BuLi; HMPA / tetrahydrofuran / 0.12 h / -78 °C

2.2: HMPA / tetrahydrofuran / 0.5 h / -78 °C

3.1: 82 percent / PPTS / 2-methyl-propan-2-ol; H₂O / 13 h / 20 °C

4.1: 58 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / various solvents / 7 h / 40 °C

5.1: 64 percent / PPTS / CH₂Cl₂ / 8 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; various solvents; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2006.04.018