(2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Base Information

• Chemical Name: (2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one
• CAS No.: 203926-66-3
• Molecular Formula: C₃₇H₅₀O₉
• Molecular Weight: 638.799

Synonyms:(2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

Chemical Property of (2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

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Technology Process of (2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

There total 18 articles about (2S,5S)-5-({(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}-hydroxy-methyl)-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:

(2R,3R)-4-(4-Methoxy-benzyloxy)-3-methyl-butane-1,2-diol (135265-40-6) → (2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one (203926-66-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / N-p-toluenesulfonyl imidazole, NaH / tetrahydrofuran

2: 87 percent / BF₃*Et₂O

3: TBAF / tetrahydrofuran

4: Et₃N

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

6: imidazole / CH₂Cl₂ / 0.75 h

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

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

9: 98 percent / TBAF / tetrahydrofuran

10: 86 percent / Dess-Martin periodinane

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

With 1H-imidazole; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-tosylimidazole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja973286p

Reference yield:

(R)-2-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxirane (135265-42-8) → (2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one (203926-66-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 87 percent / BF₃*Et₂O

2: TBAF / tetrahydrofuran

3: Et₃N

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

5: imidazole / CH₂Cl₂ / 0.75 h

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

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

8: 98 percent / TBAF / tetrahydrofuran

9: 86 percent / Dess-Martin periodinane

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

With 1H-imidazole; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja973286p

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (2S,5S)-5-({(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}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one (203926-66-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 75 percent / NaH, TBAI / tetrahydrofuran

2: 80 percent / methanolic p-TsOH

3: 87 percent / N-p-toluenesulfonyl imidazole, NaH / tetrahydrofuran

4: 87 percent / BF₃*Et₂O

5: TBAF / tetrahydrofuran

6: Et₃N

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

8: imidazole / CH₂Cl₂ / 0.75 h

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

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

11: 98 percent / TBAF / tetrahydrofuran

12: 86 percent / Dess-Martin periodinane

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

With 1H-imidazole; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-tosylimidazole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja973286p

upstream raw materials:

(2S,5S)-2-(tert-butyl)-5-methyl-1,3-dioxolan-4-one

(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

(R)-2-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxirane

(2R,3R)-4-(4-Methoxy-benzyloxy)-3-methyl-butane-1,2-diol

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