(2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran
CAS No.:79386-87-1
Molecular Formula:C₂₉H₄₆O₆
Molecular Weight:490.681
Hs Code.:

(2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

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Chemical Property of (2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

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Technology Process of (2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

There total 12 articles about (2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran 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:

: Acetic acid (1S,2S)-1-((R)-1-hydroxy-ethyl)-2-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propyl ester

: 79386-87-1
(2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / 1 h / Ambient temperature

2: 958 mg / CH₃ONa / CHCl₃; methanol / 20 h / 0 °C

3: 1.) BuLi / 1.) THF, hexane, -20 deg C, 2 h, 2.) THF, hexane, -20 deg C, 2 h, then 0-2 deg C, 4 d

4: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 0.5 h

5: HgO, HgCl₂ / acetone; H₂O / 0.33 h / 70 °C

6: 1.) BuLi / 1.) ether, hexane, -78 deg C, 1.5 h, 2.) ether, hexane, -78 to 0 deg C, 1.5 h

7: 100 percent / H₂ / palladium black / methanol / 0.12 h / Ambient temperature

8: 44 percent / H₂ / palladium black / methanol / 0.33 h / Ambient temperature

9: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 1 h

With pyridine; n-butyllithium; hydrogen; sodium methylate; sodium hydride; mercury dichloride; mercury(II) oxide; palladium; In methanol; chloroform; water; acetone;
DOI:10.1246/bcsj.54.1749

Reference yield:

: 79386-76-8,84278-12-6
2-O-benzyl-1,4,7-trideoxy-5,6-O-isopropylidene-4-C-methyl-L-glycero-D-talo-heptitol

: 79386-87-1
(2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 11 steps

1: 96 percent / DMAP / ethyl acetate / 1.5 h / Ambient temperature

2: H₂ / palladium black / methanol / 0.17 h / Ambient temperature

3: pyridine / 1 h / Ambient temperature

4: 958 mg / CH₃ONa / CHCl₃; methanol / 20 h / 0 °C

5: 1.) BuLi / 1.) THF, hexane, -20 deg C, 2 h, 2.) THF, hexane, -20 deg C, 2 h, then 0-2 deg C, 4 d

6: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 0.5 h

7: HgO, HgCl₂ / acetone; H₂O / 0.33 h / 70 °C

8: 1.) BuLi / 1.) ether, hexane, -78 deg C, 1.5 h, 2.) ether, hexane, -78 to 0 deg C, 1.5 h

9: 100 percent / H₂ / palladium black / methanol / 0.12 h / Ambient temperature

10: 44 percent / H₂ / palladium black / methanol / 0.33 h / Ambient temperature

11: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 1 h

With pyridine; dmap; n-butyllithium; hydrogen; sodium methylate; sodium hydride; mercury dichloride; mercury(II) oxide; palladium; In methanol; chloroform; water; ethyl acetate; acetone;
DOI:10.1246/bcsj.54.1749

Reference yield:

: 79391-42-7,79464-42-9
(4R,5R,6R)-2-((2R,3R,4S,6R)-4,6-Dimethoxy-3-methyl-tetrahydro-pyran-2-yl)-4-methyl-6-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hept-1-ene-3,5-diol

: 79386-87-1
(2R,3R,4S,6R)-2-[(Z)-(3S,4R,5R)-4-Benzyloxy-1,3-dimethyl-5-((4S,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-hex-1-enyl]-4,6-dimethoxy-3-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: 44 percent / H₂ / palladium black / methanol / 0.33 h / Ambient temperature

2: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 1 h

With hydrogen; sodium hydride; palladium; In methanol;
DOI:10.1246/bcsj.54.1749