(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

Base Information

Chemical Name:(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester
CAS No.:906545-78-6
Molecular Formula:C₃₉H₄₂O₈
Molecular Weight:638.758
Hs Code.:

Synonyms:(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

There total 4 articles about (S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl 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:

: ((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-2-yloxy)-acetic acid methyl ester

: 906545-78-6
(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.97 g / NaOH / methanol / 2 h / 20 °C

2: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

3: 1.60 g / diethyl ether / 0 °C

With sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; ethylbenzene; 2: <2,3>-Wittig sigmatropic rearrangement;
DOI:10.1021/ol061100y

Reference yield:

: 906545-77-5
(2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid

: 906545-78-6
(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

2: 1.60 g / diethyl ether / 0 °C

With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; n-heptane; ethylbenzene; 1: <2,3>-Wittig sigmatropic rearrangement;
DOI:10.1021/ol061100y

Reference yield:

: 352020-76-9
2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranose

: 906545-78-6
(S)-2-Hydroxy-4-[(3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidene]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 °C

2: 1.97 g / NaOH / methanol / 2 h / 20 °C

3: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

4: 1.60 g / diethyl ether / 0 °C

With sodium hydroxide; boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; ethylbenzene; 3: <2,3>-Wittig sigmatropic rearrangement;
DOI:10.1021/ol061100y