(3S,R_S)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran

Base Information

• Chemical Name: (3S,R_S)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran
• CAS No.: 113457-89-9
• Molecular Formula: C₂₅H₃₂O₅S
• Molecular Weight: 444.592
• Mol file: 113457-89-9.mol

Synonyms:(3S,R_S)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran

Chemical Property of (3S,R_S)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,R_S)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran

There total 14 articles about (3S,R_S)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran 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%

(S)-5-((S)-Benzenesulfinyl)-3-benzyloxymethyl-6-[4-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-butyl]-3,4-dihydro-2H-pyran → (3S,RS)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran (113457-89-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 7h; Ambient temperature;

DOI:10.1248/cpb.41.339

Reference yield:

(S)-3-Benzyloxymethyl-6-[4-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-butyl]-5-(toluene-4-sulfinyl)-3,4-dihydro-2H-pyran (113457-88-8,113477-01-3,148324-35-0,148324-36-1) → (3S,RS)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran (113457-89-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)96304-4

Reference yield:

diethyl 2-(3-oxo-propyl)malonate (19515-61-8) → (3S,RS)-3-benzyloxymethyl-6-<3,3-bis(hydroxymethyl)propyl>-3,4-dihydro-3-hydroxymethyl-5-(p-tolyl)sulfinyl-2H-pyran (113457-89-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) H⁽¹⁺⁾; 2.) LAH / 2.) ether

2: 1.)imidazole; 2.) p-TsOH / 2.) acetone

3: 84 percent

4: 87 percent

6: 91 percent / ZnCl₂

7: 71 percent / trifluoroacetic acid

8: (n-Bu)4NF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen cation; toluene-4-sulfonic acid; trifluoroacetic acid; zinc(II) chloride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96304-4

upstream raw materials:

(S)-3-Benzyloxymethyl-6-[4-(tert-butyl-diphenyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-butyl]-5-(toluene-4-sulfinyl)-3,4-dihydro-2H-pyran

benzyl bromide

diethyl 2-(3-oxo-propyl)malonate

(R)-methyl p-tolyl sulfoxide

Downstream raw materials:

[(3S,6R,9S,11S)-9-Benzyloxymethyl-11-((R)-toluene-4-sulfinyl)-1,7-dioxa-spiro[5.5]undec-3-yl]-methanol

Trifluoro-acetic acid (3S,4R,6S,9S)-3-benzyloxymethyl-9-ethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

Trifluoro-acetic acid (3S,4S,6R,9S)-3-benzyloxymethyl-9-ethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

(3S,6S,9S)-3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene