(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane
• CAS No.: 1063713-63-2
• Molecular Formula: C₄₀H₇₄O₇Si₃
• Molecular Weight: 751.28
• Mol file: 1063713-63-2.mol

Synonyms:(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

Chemical Property of (1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

There total 1 articles about (1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane 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: 91.0%

(1R,3S)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-3-methyl-hept-6-ene-1,3-diol (1063693-65-1) → (1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane (1063713-63-2)

Guidance literature:

(1R,3S)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-3-methyl-hept-6-ene-1,3-diol; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; for 3h;

DOI:10.1021/ol801585j

Reference yield: 45.0%

(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane (1063713-63-2) → (S)-1-((2R,4R,5S)-5-((1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl)-4-hydroxy-5-methyltetrahydrofuran-2-yl)ethane-1,2-diol + (2S,3R,5R)-2-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-5-{(S)-1-[(tert-butyldimethylsilyl)oxy]-2-hydroxyethyl}-5-methyltetrahydrofuran-3-ol + (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol (1289512-61-3)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/ejoc.201001411

Reference yield:

(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane (1063713-63-2) → ((S)-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-((2R,5R,7S)-7((S)-1-[(tert-butyldiphenylsilyl)oxy]propan-2-yl)-1,6-dioxaspiro[4.5]decan-2-yl)methoxy)(tert-butyl)dimethylsilane (1289512-98-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

2.2: 0.75 h / -30 °C / Inert atmosphere

2.3: 0.17 h / -30 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 17 h / Inert atmosphere; Reflux

5.1: pyridine; 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 4 h / Inert atmosphere

6.1: chloroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; 5% Pd(II)/C(eggshell); hydrogen; pyridine hydrogenfluoride; dimethyl sulfoxide; chloroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; 2.1: Swern oxidation / 2.2: Swern oxidation / 2.3: Swern oxidation;

DOI:10.1002/ejoc.201001411

upstream raw materials:

(1R,3S)-6-benzyloxymethyl-1-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-3-methyl-hept-6-ene-1,3-diol

Downstream raw materials:

(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

(5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one

C₆₀H₉₂O₉Si₃

(5S,6R,13S,14S)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadecan-9-one