{(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane
• CAS No.: 329359-62-8
• Molecular Formula: C₄₉H₇₃IO₁₀Si
• Molecular Weight: 977.103

Synonyms:{(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

Chemical Property of {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

There total 17 articles about {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane 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: 96.0%

(2R,3S,4R,5R)-5-Benzyloxymethoxy-6-[(2S,4S,6R,8R,10S)-8-benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(3,4-dimethoxy-benzyloxy)-2,4-dimethyl-hexan-1-ol (329359-47-9) → {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-62-8)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In acetonitrile; benzene;

DOI:10.1002/1521-3773(20010105)40:1<191::AID-ANIE191>3.0.CO;2-C

Reference yield:

(2S,4S)-5-[2-((2S,4R)-5-Benzyloxy-2,4-dihydroxy-pentyl)-[1,3]dithian-2-yl]-4-methoxy-pentane-1,2-diol → {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-62-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Hg(ClO₄)2; CaCO₃ / acetonitrile; H₂O

2.1: HClO₄ / CH₂Cl₂; acetonitrile

3.1: 87 percent / Et₃N / CH₂Cl₂

4.1: 99 percent / imidazole / dimethylformamide

5.1: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

6.1: 90 percent / I₂; PPh₃; imidazole / benzene

7.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C

7.2: 95 percent / tetrahydrofuran / -78 - 0 °C

8.1: 71 percent / Hg(ClO₄)2; CaCO₃ / methanol; H₂O / 0 °C

9.1: NaBH₄ / methanol; CH₂Cl₂

10.1: 94 percent / iPr₂NEt / CH₂Cl₂

11.1: 78 percent / DIBAL / toluene; various solvent(s) / -78 - 0 °C

12.1: 96 percent / I₂; PPh₃; imidazole / benzene; acetonitrile

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; perchloric acid; mercury(II) perchlorate; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010105)40:1<191::AID-ANIE191>3.0.CO;2-C

Reference yield:

(S)-4-((S)-3-{2-[(2S,4R)-5-Benzyloxy-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentyl]-[1,3]dithian-2-yl}-2-methoxy-propyl)-2,2-dimethyl-[1,3]dioxolane (201275-41-4) → {(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-2-Benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-6-iodo-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane (329359-62-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 85 percent / HCl / methanol

2.1: Hg(ClO₄)2; CaCO₃ / acetonitrile; H₂O

3.1: HClO₄ / CH₂Cl₂; acetonitrile

4.1: 87 percent / Et₃N / CH₂Cl₂

5.1: 99 percent / imidazole / dimethylformamide

6.1: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

7.1: 90 percent / I₂; PPh₃; imidazole / benzene

8.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C

8.2: 95 percent / tetrahydrofuran / -78 - 0 °C

9.1: 71 percent / Hg(ClO₄)2; CaCO₃ / methanol; H₂O / 0 °C

10.1: NaBH₄ / methanol; CH₂Cl₂

11.1: 94 percent / iPr₂NEt / CH₂Cl₂

12.1: 78 percent / DIBAL / toluene; various solvent(s) / -78 - 0 °C

13.1: 96 percent / I₂; PPh₃; imidazole / benzene; acetonitrile

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; perchloric acid; mercury(II) perchlorate; iodine; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010105)40:1<191::AID-ANIE191>3.0.CO;2-C

upstream raw materials:

(2R,3S,4R,5R)-5-Benzyloxymethoxy-6-[(2S,4S,6R,8R,10S)-8-benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-3-(3,4-dimethoxy-benzyloxy)-2,4-dimethyl-hexan-1-ol

tert-butyldimethylsilyl chloride

(2R,3R,4R)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol

2,2-Dimethyl-propionic acid (2S,4S,6R,8R,10S)-8-benzyloxymethyl-10-hydroxy-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Downstream raw materials:

{(2R,4S,6R,8S,10S)-8-[(2R,3R,4R,5S)-6-Benzenesulfonyl-2-benzyloxymethoxy-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexyl]-2-benzyloxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy}-tert-butyl-dimethyl-silane

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