(3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol

Base Information

• Chemical Name: (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol
• CAS No.: 634587-01-2
• Molecular Formula: C₃₃H₆₁NO₅Si
• Molecular Weight: 579.937
• Mol file: 634587-01-2.mol

Synonyms:(3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol

Chemical Property of (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol

There total 15 articles about (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol 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: 65.0%

{(Z)-(S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-heptadec-2-enyl}-carbamic acid benzyl ester (634586-98-4) → (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol (634587-01-2) + (3S,4R,5S)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol (634587-04-5)

Guidance literature:

With methanesulfonamide; AD-mix-β; In water; tert-butyl alcohol; at 0 - 20 ℃; for 48h;

Reference yield:

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde (634586-95-1) → (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol (634587-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / tetrahydrofuran

2: AD-mix-β

With AD-mix-β; In tetrahydrofuran; 2: Sharpless dihydroxylation;

DOI:10.1002/anie.200454215

Reference yield:

pentadecyltriphenylphosphonium bromide (1944-80-5) → (3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol (634587-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hexamethyldisilazide / tetrahydrofuran / -75 °C

2: 85 percent / tetrahydrofuran

3: AD-mix-β

With AD-mix-β; sodium hexamethyldisilazane; In tetrahydrofuran; 3: Sharpless dihydroxylation;

DOI:10.1002/anie.200454215

upstream raw materials:

{(Z)-(S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-heptadec-2-enyl}-carbamic acid benzyl ester

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde

pentadecyltriphenylphosphonium bromide

benzyl chloroformate

Downstream raw materials:

[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-iodo-propyl]-carbamic acid benzyl ester

(3S,4S,5R)-3-Benzylamino-1-((2R,3S,4S,5S,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol