(3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol

Base Information

Chemical Name:(3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol
CAS No.:862718-91-0
Molecular Formula:C₄₈H₆₂O₁₀S
Molecular Weight:831.08
Hs Code.:

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

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Chemical Property of (3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol

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

There total 12 articles about (3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol 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: 94.0%

: 862718-90-9
(R)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-1-ol

: 124-63-0
methanesulfonyl chloride

: 862718-91-0
(3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃;
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

: 862718-91-0
(3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol

Guidance literature:: Multi-step reaction with 5 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

4: 91 percent / TsNHNH₂; aq. NaOAc / 1,2-dimethoxy-ethane / Heating

5: 94 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; n-butyllithium; oxalyl dichloride; hydrogen; sodium acetate; dimethyl sulfoxide; toluene-4-sulfonic acid hydrazide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; 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

: 862718-91-0
(3R,4R,5R)-4,5-O-isopropylidene-3-O-methanesulfonyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3,4,5-decanetriol

Guidance literature:: Multi-step reaction with 7 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

6: 91 percent / TsNHNH₂; aq. NaOAc / 1,2-dimethoxy-ethane / Heating

7: 94 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; sodium periodate; n-butyllithium; oxalyl dichloride; hydrogen; sodium acetate; dimethyl sulfoxide; toluene-4-sulfonic acid hydrazide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; 2: Wittig reaction / 4: Swern oxidation;
DOI:10.1016/j.tetlet.2005.05.069