152386-84-0

Basic information

• Product Name: (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol
• Synonyms: (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol
• CAS NO: 152386-84-0
• Molecular Weight: 242.272
• Mol File: 152386-84-0.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol(152386-84-0)
• EPA Substance Registry System: (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol(152386-84-0)

Safety Data

• Hazardous Substances Data: 152386-84-0(Hazardous Substances Data)

Upstream product

• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 135972-13-3 (2S,3S)-2,3-O-(4-methoxybenzylidene)-diethyl tartrate 
• 152386-83-9 [(4R,5R)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-methanol 

Downstream Products

• 152386-87-3 (2S)-2-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-2-(4-methoxybenzyloxy)-acetaldehyde 
• 247221-10-9 (3R)-3-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-3-(4-methoxybenzyloxy)propene 
• 247221-12-1 (3R)-3-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-3-(4-methoxybenzyloxy)propanal 
• 247221-11-0 (3R)-3-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-3-(4-methoxybenzyloxy)propan-1-ol 
• 247221-13-2 (4R)-4-phenylmethyl-3-[[(5R)-5-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]]-(2R,3R)-3-hydroxy-5-(4-methoxybenzyloxy)-2-methyl-pentanoyl]-oxazolidin-2-one 
• 1402588-67-3 C₁₁H₁₄O₄ 
• 866454-46-8 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enoic acid 
• 866454-55-9 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-en-1-ol 
• 866454-54-8 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-en-1-ol 
• 866454-58-2 3-methoxy-2-(4-methoxybenzyloxy)-5-methylhex-5-enal 
• 1402588-85-5 C₅₈H₈₇NO₁₃Si₂ 
• 1402588-84-4 C₅₁H₈₃NO₁₂Si₂ 
• 1402589-26-7 C₅₁H₈₃NO₁₂Si₂ 
• 152386-90-8 Methanesulfonic acid (E)-(1R,2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl ester 

Relevant articles and documents

Synthesis and disproof of the structure proposed for the tetrahydrofuranol isolated from Michelia compressa var. lanyuensis (Magnoliaceae)

The previously proposed structure for a tetrahydrofuranol isolated from the leaves of Michelia compressa var. lanyuensis (Magnoliaceae) was synthesised in an enantiopure form using diethyl D-tartarate as the starting material. The synthetic sample showed spectroscopic data incompatible with those for the natural product and thus unequivocally disproved the previously assigned structure.

An aldol approach to a building block corresponding to the C21-C26-part of FK506

Starting from D-tartrate 2, the chiral aldehyde 10 was prepared in 8 steps. Key steps include the reductive opening of the p-methoxybenzyl acetal 4 and the elongation of the aldehyde 7 via Wittig and hydroboration reaction providing the alcohol 9. Subsequent Evans aldol reaction provided compound 12 which corresponds to the C21-C26 part of the immunosuppressive FK506. Wiley-VCH Verlag GmbH, 1999.

An enantiospecific synthesis of D-erythro-sphingosine from D-tartaric acid

An efficient enantiospecific synthesis of D-erythro-sphingosine (1) via azidosphingosine (2) is described, the absolute stereochemistry being derived from D-tartaric acid.