(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Base Information

Chemical Name:(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol
CAS No.:164215-43-4
Molecular Formula:C₃₅H₆₀O₈Si₂
Molecular Weight:665.028
Hs Code.:

(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Synonyms:(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Suppliers and Price of (1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

There total 18 articles about (1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol 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: 84.0%

: 164215-42-3
2,2-Dimethyl-propionic acid (1S,3R,4S,5R,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

: 164215-43-4
(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Guidance literature:: With diisobutylaluminium hydride; In toluene;
DOI:10.1021/ja00102a074

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 164215-43-4
(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) OsO₄, NMO, (DHQD)2PHAL, 2.) methanolic HCl, 3.) Et₃N, DMAP

2: 97 percent / DMAP / CH₂Cl₂ / 50 °C

3: 99 percent / H₂ / Pd(OH)2/C, Pd/CaCO₃

4: 90 percent / (COCl)2, DMSO / CH₂Cl₂

5: 78 percent / Me₃N / diethyl ether

6: 95 percent / AgNO₃, 2,6-lutidine

7: 84 percent / DIBAL-H / toluene

With 2,6-dimethylpyridine; hydrogenchloride; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; hydrogen; diisobutylaluminium hydride; silver nitrate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; trimethylamine; palladium dihydroxide; Lindlar's catalyst; calcium carbonate; In diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00102a074

Reference yield:

: 164215-29-6
(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-but-3-yne-1,2-diol

: 164215-43-4
(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Guidance literature:: Multi-step reaction with 13 steps

1: Et₃N, DMAP

2: Et₃N / CH₂Cl₂

3: 1.) n-BuLi, LiBr / 1.) THF, 2.) THF

4: 93 percent / Dess-Martin oxidant

5: 60 percent / aq. Cr(OAc)2 / tetrahydrofuran / 65 °C

6: 93 percent / Bu₄NF / tetrahydrofuran

7: 1.) OsO₄, NMO, (DHQD)2PHAL, 2.) methanolic HCl, 3.) Et₃N, DMAP

8: 97 percent / DMAP / CH₂Cl₂ / 50 °C

9: 99 percent / H₂ / Pd(OH)2/C, Pd/CaCO₃

10: 90 percent / (COCl)2, DMSO / CH₂Cl₂

11: 78 percent / Me₃N / diethyl ether

12: 95 percent / AgNO₃, 2,6-lutidine

13: 84 percent / DIBAL-H / toluene

With 2,6-dimethylpyridine; hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; chromium(II) acetate; Dess-Martin periodane; silver nitrate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; trimethylamine; palladium dihydroxide; Lindlar's catalyst; calcium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00102a074