((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 329359-34-4
• Molecular Formula: C₂₅H₄₁IO₅Si
• Molecular Weight: 576.588

Synonyms:((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of ((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane

There total 8 articles about ((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-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: 90.0%

[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-methanol (329359-60-6) → ((2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane (329359-34-4)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In 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,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane (329359-34-4)

Guidance literature:

Multi-step reaction with 6 steps

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

2: HClO₄ / CH₂Cl₂; acetonitrile

3: 87 percent / Et₃N / CH₂Cl₂

4: 99 percent / imidazole / dimethylformamide

5: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

6: 90 percent / I₂; PPh₃; imidazole / benzene

With 1H-imidazole; perchloric acid; mercury(II) perchlorate; iodine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; calcium carbonate; In dichloromethane; water; N,N-dimethyl-formamide; 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,6S,8S,10S)-2-Benzyloxymethyl-8-iodomethyl-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy)-tert-butyl-dimethyl-silane (329359-34-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / HCl / methanol

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

3: HClO₄ / CH₂Cl₂; acetonitrile

4: 87 percent / Et₃N / CH₂Cl₂

5: 99 percent / imidazole / dimethylformamide

6: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

7: 90 percent / I₂; PPh₃; imidazole / benzene

With 1H-imidazole; hydrogenchloride; perchloric acid; mercury(II) perchlorate; iodine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; calcium carbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

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

upstream raw materials:

[(2S,4S,6R,8R,10S)-8-Benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1,7-dioxa-spiro[5.5]undec-2-yl]-methanol

tert-butyldimethylsilyl chloride

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

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

Downstream raw materials:

[(2R,4S,6R,8S,10S)-2-Benzyloxymethyl-8-(2-{(S)-1-[(4S,5R)-2-(3,4-dimethoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-ethyl}-[1,3]dithian-2-ylmethyl)-10-methoxy-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane

{(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

(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

{(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

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