(2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

Base Information

Chemical Name:(2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate
CAS No.:864712-70-9
Molecular Formula:C₅₀H₇₂O₈Si₂
Molecular Weight:857.288
Hs Code.:

Synonyms:(2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

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Chemical Property of (2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

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Technology Process of (2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

There total 15 articles about (2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate 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: 100.0%

: 887768-95-8
(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate

: (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-12-(tert-butyl-diphenyl-silanyloxy)-2,3-dihydroxy-6-methyl-6-triethylsilanyloxy-dodecanoic acid methyl ester

: 864712-70-9
(2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

Guidance literature:: With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; tert-butyl alcohol; at 0 - 20 ℃; for 40h;
DOI:10.1246/bcsj.79.468

Reference yield:

: 864712-67-4
(2R,3R,4R)-2,3-bis(benzyloxy)-10-t-butyldiphenylsiloxy-4-triethylsiloxy-4-methyldecanal

: 864712-70-9
(2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / benzene / 13 h / 100 °C

2: 100 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 40 h / 0 - 20 °C

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; tert-butyl alcohol; benzene; 1: Wittig reaction;
DOI:10.1246/bcsj.79.468

Reference yield:

: 864712-68-5
3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

: 864712-70-9
(2S,3S,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-2,3-dihydroxy-6-methyldodecanoate

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / 9-BBN / tetrahydrofuran / 16 h / 20 °C

2: 1.40 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 2.37 g / n-BuLi / tetrahydrofuran; hexane / 13 h / 20 °C

4: 2.38 g / H₂ / Pd-C / ethanol / 4 h

5: Et₂O*BF₃ / acetic anhydride / 0.5 h / -25 °C

6: K₂CO₃ / methanol / 3.5 h / 20 °C

7: 2.61 g / NaBH₄ / methanol / 2 h / 20 °C

8: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

10: 100 percent / benzene / 13 h / 100 °C

11: 100 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 40 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetic anhydride; acetone; tert-butyl alcohol; benzene; 3: Wittig reaction / 9: Swern oxidation / 10: Wittig reaction;
DOI:10.1246/bcsj.79.468