(2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

Base Information

Chemical Name:(2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol
CAS No.:115275-09-7
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:

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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 (2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

Chemical Property:

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Technology Process of (2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

There total 2 articles about (2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol 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:

: 115275-07-5
diethyl (2R,3R)-2,3-O-((E)-crotylidene)tartrate

: 115275-09-7
(2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 3.5 h / 0 °C

2: 1.) NaH / 1.) DMF, THF, from 0 deg C to room temp., 1.5 h, 2.) from -20 deg C to room temp., 2 h

With sodium tetrahydroborate; sodium hydride; In methanol;
DOI:10.3987/COM-89-S70

Reference yield:

: 115275-08-6
[(4S,5S)-5-Hydroxymethyl-2-((E)-propenyl)-[1,3]dioxolan-4-yl]-methanol

: 100-39-0
benzyl bromide

: 115275-09-7
(2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

Guidance literature:: With sodium hydride; Yield given. Multistep reaction; 1.) DMF, THF, from 0 deg C to room temp., 1.5 h, 2.) from -20 deg C to room temp., 2 h;
DOI:10.3987/COM-89-S70

Reference yield:

: 115275-09-7
(2S,3S)-1-O-benzyl-2,3-O-<(E)-crotylidene>threitol

: 115275-15-5
Toluene-4-sulfonic acid (1R,3aS,4S,7aR)-4-methyl-6-oxo-hexahydro-furo[3,4-c]pyran-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) diisobutylaluminum hydride, 2.) 28percent NH₄OH / 1.) toluene, 0 deg C, 1 h, 2.) THF, MeOH, room temp., 15 d

2: aq. NaIO₄ / methanol / 2 h / 0 °C

3: ethylenediammonium diacetate / propan-2-ol / 1.) 0 deg C, 2 h, 2.) room temp., 13 h

4: dioxane; H₂O / 3.5 h

5: 4.20 g / H₂, concd HCl / 10percent Pd/C / ethanol / 5.5 h / 760 Torr / Ambient temperature

6: pyridine / 10 h / Ambient temperature

With pyridine; hydrogenchloride; ammonium hydroxide; sodium periodate; hydrogen; diisobutylaluminium hydride; ethylenediamine diacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; water; isopropyl alcohol;
DOI:10.3987/COM-89-S70