[(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester
• CAS No.: 208767-20-8
• Molecular Formula: C₃₄H₄₇NO₆Si
• Molecular Weight: 593.836
• Mol file: 208767-20-8.mol

Synonyms:[(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester

Chemical Property of [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester

There total 2 articles about [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester 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: 88.0%

[(E)-(S)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-carbamic acid tert-butyl ester (208767-19-5) → [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester (208767-20-8)

Guidance literature:

With AD-mix-β; In water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(97)10855-3

Reference yield:

(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid (208767-18-4) → [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester (208767-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) N-methylmorpholine, ClCOOiBu, 2) N-hydroxythiopyridone Na salt, 3) tert-butylmercaptane / 1) THF, -20 deg C, 20 min, 2) THF, -20 deg C, 3) THF, RT, 45 min, irradiation

2: 88 percent / OsO₄, K₂CO₃, K₃, methanesulfonamide, (DHQD)2PHAL / toluene; H₂O; 2-methyl-propan-2-ol / Ambient temperature

With 4-methyl-morpholine; osmium(VIII) oxide; methanesulfonamide; N-hydroxythiopyridone Na salt; potassium carbonate; 2-methylpropan-2-thiol; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); isobutyl chloroformate; In water; toluene; tert-butyl alcohol;

DOI:10.1002/(sici)1099-0690(199806)1998:6<1155::aid-ejoc1155>3.0.co;2-g

Reference yield: 94.0%

acetone (67-64-1) + [(2S,3R,4R)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydroxy-pentyl]-carbamic acid tert-butyl ester (208767-20-8) → {(S)-3-Benzyloxy-2-[(4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propyl}-carbamic acid tert-butyl ester (202979-48-4)

Guidance literature:

With phthalic acid dimethyl ester; toluene-4-sulfonic acid;

DOI:10.1016/S0040-4039(97)10855-3

upstream raw materials:

[(E)-(S)-2-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-carbamic acid tert-butyl ester

(E)-(2R,3S)-3-Benzyloxymethyl-2-tert-butoxycarbonylamino-6-(tert-butyl-diphenyl-silanyloxy)-hex-4-enoic acid

Downstream raw materials:

{(S)-3-Benzyloxy-2-[(4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propyl}-carbamic acid tert-butyl ester

(3aR,7S,7aR)-7-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine

[(S)-3-Benzyloxy-2-((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid tert-butyl ester