(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

Base Information

Chemical Name:(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol
CAS No.:862718-88-5
Molecular Formula:C₄₇H₅₆O₈
Molecular Weight:748.957
Hs Code.:

Synonyms:(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

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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 (3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

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Technology Process of (3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

There total 9 articles about (3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol 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: 47.0%

: 132015-82-8
(2R,3R)-2,3-isopropylidenedioxyoctanal

: 287962-77-0
(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyl-tetrahydropyran

: (3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

: 862718-88-5
(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -48 - -30 ℃;
DOI:10.1016/j.tetlet.2005.05.069

Reference yield:

: 862718-87-4
[(4S,5R)-2,2-Dimethyl-5-((Z)-pent-1-enyl)-[1,3]dioxolan-4-yl]-methanol

: 862718-88-5
(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / ethanol / 20 °C

2: 80 percent / DMSO; (COCl)2 / CH₂Cl₂ / -78 - 0 °C

3: 47 percent / n-BuLi / tetrahydrofuran / -48 - -30 °C

With n-butyllithium; oxalyl dichloride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 2: Swern oxidation;
DOI:10.1016/j.tetlet.2005.05.069

Reference yield:

: 73209-96-8
(S)-1-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol

: 862718-88-5
(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1: NaIO₄ / H₂O / 20 °C

2: 79 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

3: 96 percent / H₂ / Pd/C / ethanol / 20 °C

4: 80 percent / DMSO; (COCl)2 / CH₂Cl₂ / -78 - 0 °C

5: 47 percent / n-BuLi / tetrahydrofuran / -48 - -30 °C

With sodium periodate; n-butyllithium; oxalyl dichloride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; 2: Wittig reaction / 4: Swern oxidation;
DOI:10.1016/j.tetlet.2005.05.069