(5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol

Base Information

• Chemical Name: (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol
• CAS No.: 202062-72-4
• Molecular Formula: C₄₄H₅₆O₇Si
• Molecular Weight: 725.01

Synonyms:(5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol

Chemical Property of (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol

There total 10 articles about (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol 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: 73.0%

2,2-dimethoxy-propane (77-76-9) + (1S,2S,4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxymethyl-5-(4-methoxy-benzyloxymethyl)-5-methyl-cyclohexane-1,2-diol (202062-63-3) → (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol (202062-72-4)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)10554-8

Reference yield:

benzyl bromide (100-39-0) → (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol (202062-72-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / nBu₄NI, KH / tetrahydrofuran / Ambient temperature

2: 84 percent / SeO₂, 70percent TBHP, salicylic acid / CH₂Cl₂ / 12 h / Ambient temperature

3: 82 percent / OsO₄, Me₃NO / acetone; H₂O / 36 h / Ambient temperature

4: 97 percent / DMAP / CH₂Cl₂ / 0 deg C up to RT

5: 96 percent / CSA / CH₂Cl₂ / Ambient temperature

6: LiAlH₄ / diethyl ether / 1 h / 0 deg C up to RT

With tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; selenium(IV) oxide; trimethylamine-N-oxide; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium hydride; salicylic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(97)10554-8

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (5S,6S,8S,9R,10R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxymethyl)-9-(4-methoxy-benzyloxymethyl)-2,2,9-trimethyl-1,3-dioxa-spiro[4.5]decan-6-ol (202062-72-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

2: 69 percent / BF₃*OEt₂, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 °C

3: LiAlH₄ / diethyl ether / 1 h / 0 deg C up to RT

4: 97 percent / imidazole / CH₂Cl₂ / 0 deg C up to RT

5: 99 percent / nBu₄NI, KH / tetrahydrofuran / Ambient temperature

6: 84 percent / SeO₂, 70percent TBHP, salicylic acid / CH₂Cl₂ / 12 h / Ambient temperature

7: 82 percent / OsO₄, Me₃NO / acetone; H₂O / 36 h / Ambient temperature

8: 73 percent / CSA / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; osmium(VIII) oxide; lithium aluminium tetrahydride; selenium(IV) oxide; trimethylamine-N-oxide; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; salicylic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(97)10554-8

upstream raw materials:

2,2-dimethoxy-propane

(1S,2S,4S,5R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxymethyl-5-(4-methoxy-benzyloxymethyl)-5-methyl-cyclohexane-1,2-diol

benzyl bromide

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

[(5S,6R,7R,8S,10S)-8,10-Bis-benzyloxy-7-(4-methoxy-benzyloxymethyl)-2,2,7-trimethyl-1,3-dioxa-spiro[4.5]dec-6-ylmethoxy]-tert-butyl-diphenyl-silane

[(5S,6R,7R,8S,10S)-8,10-Bis-benzyloxy-7-(4-methoxy-benzyloxymethyl)-2,2,7-trimethyl-1,3-dioxa-spiro[4.5]dec-6-yl]-methanol

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