(4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

Base Information

• Chemical Name: (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine
• CAS No.: 441044-67-3
• Molecular Formula: C₄₆H₅₇NO₈S
• Molecular Weight: 784.026
• Mol file: 441044-67-3.mol

Synonyms:(4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

Chemical Property of (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

There total 6 articles about (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine 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: 71.0%

(S)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine (246864-27-7) + 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol (246864-26-6) → (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine (441044-67-3)

Guidance literature:

With potassium carbonate; In acetone; for 4.4h; Heating;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine (441044-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄

2: NaOMe

3: K₂CO₃ / acetonitrile; methanol / Heating

With sodium tetrahydroborate; sodium methylate; potassium carbonate; In methanol; acetonitrile; 1: Reduction / 2: Deacetylation / 3: Alkylation;

DOI:10.1039/a905014k

Reference yield:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → (4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine (441044-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / methanol

2: 83 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 1 h / 0 °C

3: 57 percent / NaOMe / methanol / 4 h

4: 71 percent / K₂CO₃ / acetone / 4.4 h / Heating

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; sodium methylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; acetone;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Downstream raw materials:

[(R)-1-Hydroxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester

5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-decitol

(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

methyl 5,9-andhydro-6,7,8,10-tetra-O-benzyl-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-deconate