(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester
CAS No.:98050-51-2
Molecular Formula:C₂₉H₄₀O₈Se
Molecular Weight:595.592
Hs Code.:

(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

Synonyms:(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

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Chemical Property of (3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

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Technology Process of (3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

There total 9 articles about (3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic 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: 65.0%

: 71098-88-9
N-phenylselanylphthalimide

: 98050-46-5
methyl <1,2-O-isopropylidene-β-L-threo-tetrofurano>-<3,4-f>-(3R,4S,5S,1'R)-4-<4-<(tetrahydropyranyl)oxy>-1-hydroxybutyl>-3-(hydroxymethyl)cyclohexane-5-carboxylate

: 98050-51-2
(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

Guidance literature:: With tributylphosphine; In tetrahydrofuran; at 0 ℃; for 4h;
DOI:10.1021/jo00224a024

Reference yield:

: 6089-04-9
3-(tetrahydropyran-2'-yloxy)propyne

: 98050-51-2
(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) EtMgBr / 1.) Et₂O, THF, RT, 2.) Et₂O, THF, 0-2 deg C, overnight

2: 77 percent / H₂ / PtO₂ / methanol; tetrahydrofuran / 5 h / 760 Torr

3: aq. KOH / methanol / 1.5 h / Heating

4: NaBH₄ / methanol / 1.5 h / 0 °C

5: tetrahydrofuran; diethyl ether / 1 h / 0 °C

6: 65 percent / n-Bu₃P / tetrahydrofuran / 4 h / 0 °C

With potassium hydroxide; sodium tetrahydroborate; tributylphosphine; ethylmagnesium bromide; hydrogen; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/jo00224a024

Reference yield:

: 81049-53-8
3,5,6-Trideoxy-3,5(E)-dieno-1,2-O-isopropylidene-α-D-glycero-heptofuranose

: 98050-51-2
(3aR,4aR,6S,7R,8R,8aS,8bR)-2,2-Dimethyl-6-phenylselanylmethyl-7-[4-(tetrahydro-pyran-2-yloxy)-butyryl]-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-8-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: diethyl ether / 30 h / Ambient temperature

2: tetrahydrofuran

3: 1.) EtMgBr / 1.) Et₂O, THF, RT, 2.) Et₂O, THF, 0-2 deg C, overnight

4: 77 percent / H₂ / PtO₂ / methanol; tetrahydrofuran / 5 h / 760 Torr

5: aq. KOH / methanol / 1.5 h / Heating

6: NaBH₄ / methanol / 1.5 h / 0 °C

7: tetrahydrofuran; diethyl ether / 1 h / 0 °C

8: 65 percent / n-Bu₃P / tetrahydrofuran / 4 h / 0 °C

With potassium hydroxide; sodium tetrahydroborate; tributylphosphine; ethylmagnesium bromide; hydrogen; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1021/jo00224a024