(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Base Information

Chemical Name:(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one
CAS No.:194039-03-7
Molecular Formula:C₃₇H₅₀O₈
Molecular Weight:622.799
Hs Code.:

(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Synonyms:(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

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Chemical Property of (2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

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Technology Process of (2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

There total 21 articles about (2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 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:

: Dithiocarbonic acid O-[{(2S,5R,6S,8S)-5-benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-methyl] ester S-methyl ester

: 194039-03-7
(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 2h; Yield given;
DOI:10.1021/ja973286p

Reference yield:

: 203926-64-1
(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

: 194039-03-7
(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 15 min

2: 1.) NaH

3: n-Bu₃SnH, AIBN / toluene / 2 h / 80 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; lithium diisopropyl amide; In toluene;
DOI:10.1021/ja973286p

Reference yield:

: 194038-95-4
{(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane

: 194039-03-7
(2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 40 min

2: imidazole / CH₂Cl₂ / 0.75 h

3: 1.) CuI / 1.) Et₂O, from -78 to -40 deg C, 2.) Et₂O, -78 deg C, 2.5 h

4: p-TsOH*H₂O / benzene / 11 h / Ambient temperature

5: 98 percent / TBAF / tetrahydrofuran

6: 86 percent / Dess-Martin periodinane

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 15 min

8: 1.) NaH

9: n-Bu₃SnH, AIBN / toluene / 2 h / 80 °C

With 1H-imidazole; copper(l) iodide; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/ja973286p